FRONT MATTER

SECTION 1

Thank You 1Password

This book is a gift, courtesy of the folks at 1Password, the best

password management solution. While you are getting better at
your email, don’t forget to secure your passwords.

2
 SECTION 2

A Note from Dave at 1Password

To all our amazing customers. We wouldn't be here without you.
Thank you for enabling us to work at our dream jobs.
–Dave Teare

3
 SECTION 3

Dedication

To Alisa, with much love.

4
 SECTION 4

Acknowledgements

You get a cookie. Merlin Mann, David Allen, and E. B.

White. My thanks also go to the hard-
So many people helped make this book
working software developers and engineers
possible. First, I want to thank my family.
who made the great email applications and
Daisy, Samantha, and Sarah were all
services that make taming email
troopers, letting me spend countless
possible. I did not include
hours researching, writing, and
anything in this book that I
screencasting to make this book
didn’t feel was useful and a
possible.
potential solution for my
I also want to thank the readers.
many teachers I’ve had
For some time, I’ve
along the path as I
admired Mike
figured out how to deal
Rohde’s sketches.
with email, including
I’m thrilled that he

5
agreed to illustrate this book. Darren Rolfe Finally, thank you MacSparky readers and
has helped me with every cover of the Mac Power Users listeners. I cannot
MacSparky Field Guides and for that I’m overstate how much love and appreciation I
eternally grateful. I’d also like to thank my have for each and every one of you.
principal proofreader, Leilani Resurreccion.



David Sparks, November 12, 2013
I also had an intrepid group of friends that
offered their time and feedback including
J.F. Brissette, Jean MacDonald, and Eddie
Smith.

There is also a group of people at Apple that

built the iBooks Author tools and manage
the iBooks Store. I’m one of the smallest
publishers in the iBooks Store but they
don’t treat me that way. These books would
simply not exist without the hard work of
the entire iBooks team.

6
 SECTION 5

About David Sparks

David Sparks is a Paperless, Markdown, and 60

productivity con man who Mac Tips. David also wrote
claims to help you get more two previous books, Mac at
efficient with your technology Work and iPad at Work, which
but can just as easily wreck a lot of people seemed to like.
your day with some bit of
David cohosts the Mac Power
fiddly awesomeness. David
Users podcast (website)
publishes MacSparky.com
where he, along with Katie
(website), where he writes
Floyd (website), routinely
about getting the most out of Apple
tackles technology and workflows in
technologies. Additionally, David
excruciating detail. David also speaks about
contributes to Macworld magazine (website).
technology at places such as Macworld/
David writes and publishes the MacSparky
iWorld and the American Bar Association.
Field Guides (website) that include

7
When David isn’t speaking and writing
about technology, he practices law in
Orange County, California, and spends his
time with his wife and two daughters.

8
 SECTION 6

The MacSparky Field Guides

The MacSparky Field Guides exist to turn their
The MacSparky readers into bad-ass wielders of technology. The MacSparky
Field Guide series Field Guide series
-Official Mission Statement
is a nutty idea are intended to be
cooked up by the Pixar movies of
David Sparks to publish quality, tech books with
exhaustive guides for getting the excellent execution,
most from your Apple cutting-edge technology,
technologies. They are and, at the end of the day,
intended as a soup-to-nuts a good story for the
explanation for people who reader. Throughout the
want to get some serious work Field Guide series, David
done. These books go into Sparks demonstrates
glorious, agonizing detail about workflows and applications to
practical technology solutions. help you along.

9
This book is a mixture of finely crafted
words, photo galleries, interactive images,
screencasts, and audio interviews all
designed to make you the boss of your
email. There is nearly an hour-and-a-half of
video in this “book”. You, my friend, are
about to receive your email black belt.

10
 Most presentations are
terrible. That, however,
does not need to be the
case for your
presentations. This
Presentation Field Guide
explains how to plan a
presentation that will
connect with your audience, the technical
wizardry to create a stunning presentation,
and walks you through presentation day to
make sure it goes off without a hitch. The
material is accessible to beginners and
power users alike with a thoughtful, fun,
and systematic approach to planning,
1 of 12 creating, and delivering a stellar
presentation. There’s even a video.
(website)

11
 Paperless takes the mystery (and fear) out of
going paperless with your Apple technology.
The material is accessible to beginners and
power users alike with a thorough
explanation of all the hardware, software,
and workflows necessary to finally conquer
paper.

12
Markdown started as a clever way to write for
the web but has become so much more. This
book demystifies Markdown, making it easy
for anybody to learn. You can go from no
knowledge to Markdown pro. It will change
the way you write forever.

1 of 11

13
 60 Mac Tips is a carefully built list of tips and
tricks to make you more efficient on your
Mac. The book explains why each trick is
special and most include a screencast showing
you how to perform it on your very own Mac.
Carefully paced, this book takes intermediate
and beginner Mac users and turns them into
Mac power users.

14
 SECTION 7

How to Read This Book

This “book” is a photos from the iBooks version but not in

brave new the self-contained iBooks format. Instead,
venture into a this PDF download includes the PDF file,
multimedia which you are now reading, and several
something. This folders with all of the screencasts and photo
book is sold in the galleries from this book. There are several
iBooks format screenshots of videos in this book but in
through the Apple order to see the videos themselves, go to the
iBooks Store for the accompanying folders.
Mac and iPad and as a
PDF file. This is the A BRIEF WORD ABOUT LINKS
PDF version. The PDF
There are several links in this book that take
version includes all the
you to websites, app stores, Twitter,
movies and gallery
Wikipedia, and YouTube. For some readers,

15
these external links are jarring in that they
take you out of this PDF and in and into
some other application on your Mac or iPad.
I put these links in parentheses or brackets
so you, dear reader, know when you are
about to kick yourself out of this book.
Want to see how that works? Press this
(YouTube).

Now let’s go tackle email together.

16
 SECTION 8

Email Field Guide Update Log

Every MacSparky Field Guide gets free ❖ Added new section on Apple Mail Drop.
updates for two years after its initial
❖ Added new section and screencast on the
publication date. (This book was originally
Apple Mail Markup Extension.
published in November 2013.) My goal is to
keep the book current with the latest ❖ Added new section and screencast on
workflow updates, apps, and technologies. minimizing draft messages on iPad and
Here is a list of the changes. iPhone.

❖ Updated section on Swipe Options based

VERSION 1.2, NOVEMBER 2014
on iOS 8 improvements.
❖ Added additional Gmail backup solution,
Backupify ❖ Added an explanation of Apple Mail
Handoff.
❖ Added Google Takeout to archiving
chapter.

17
❖ Added a new section for VIP Threads in ❖ Converted Email Port list into a table
Apple Mail.
❖ Added Apple Mail archive keyboard
❖ Added Key Rocket for Gmail Chrome combination
extension
❖ Rewrote the description of MailMate
❖ Added bacn remover Unroll.me based on recent developments

❖ Updated for Microsoft Outlook 2014 ❖ Added additional screenshots to the

Outlook Gallery
❖ I topped the coolant and wiper fluid
❖ Added explanation of yearly archives
VERSION 1.1, DECEMBER 2013 ❖ Added an explosion video sans
❖ 100% better controls on the audio advertisement
interviews
❖ Squashed typos
❖ Fixed my misguided confusion between
❖ Added 1.21 jigawatts to the the flux
carbon paper and mimeograph
capacitor
❖ Fixed Screencast 4.20

❖ Changed the recommended write order VERSION 1.0, NOVEMBER 2013

to add recipient last “It’s Alive!” (YouTube)

18
 CHAPTER 1

THE EMAIL
PROBLEM
 SECTION 1

The Email Problem

museum a collection of richly composed

correspondence between loved ones and
not-so-loved ones that really give you a
I’ve window into their world and thoughts. I
always even saw this with my own parents’
had this correspondence. With the advent of the
thing for the telephone, however, that all changed. Most
way people people of my generation never got into the
used to write habit of writing letters to one another. We
letters to called each other on the telephone (and now
one another. we text). It always felt to me as if we left
Look at something special behind.
anybody worth remembering from the
beginning of recorded history to the Then email arrived.
mid-20th century and you will find in some
20
I got my first email account in 1988. As a got sloppy. Even worse, there was a lot
nerd with a closet letter fetish, it seemed more of it and I began to let email run my
that email was the perfect solution. So I life.
started looking for friends with email
Then I started writing books, producing
accounts whom I could write with Winston
podcasts, and otherwise putting myself out
Churchill-calibre aplomb. In those first few
there. The email problem that I was barely
years I wrote some real doozies. Before long
managing blew up in my face. I can even tell
however, my email correspondence became
you the exact moment that I realized my
decidedly less archival and much more
email problem was out of control. It was
practical. Moreover, my email
shortly after Paperless was released and I
correspondents shifted from my dearest
was working through a big stack of emails.
friends to people interested in helping me
It was becoming a daily chore for me. For
get rid of my pesky cash for highly dubious
hours every day, I was digging myself out
products, services, and “enhancement”
while sitting on the couch. During the same
drugs.
period my 11-year-old daughter was
This transition was gradual and unexpected. building something with a particularly
At some point, I became conscious of it and daunting set of LEGO bricks. So that’s how
slowly my attitude (and enthusiasm) toward it was: Dad emailed, Sarah built. I finally
email changed for the worse. My emails responded to the last email and looked down
became much shorter and my email habits to see Sarah had finished with her LEGO

21
set. I didn’t get to help her with a single Mr. White. He was carpet-bombed with
brick. As if on cue, I then received an email letters and responding to this mail (not
from a reader who chastised me for not writing more books) took all of his time. (E.
responding to her email that she sent six B. White did not publish another children’s
days earlier. It read: “Since you don’t take book until 1973.) He became so frustrated
email seriously, I recommend you remove with the mail that he somewhat in jest asked
your email address from your website.” My one young correspondent to “start a
reaction was not subtle (YouTube). movement in America called ‘Don’t write to
E. B. White until he produces another
This problem is
book.’”
not new. E. B.
White wrote When a school librarian saw his response,
Charlotte’s Web in she wrote to him complaining. E. B. White
1952 (Wikipedia). replied, explaining how the practice of
I think everyone having all of these children write to him was
could agree it was overwhelming. He went on to explain how
a pretty good he had an idea for a new novel and had
E.B. White
book. The trouble started working on it but was unable to
was that every begin writing in earnest because when he
teacher and librarian in the country started looked at his desk, all he could see were “the
instructing schoolchildren to send letters to unanswered letters and the undone things

22
 E. B. White: The morning mail is my enemy.
[that] lie in accusing piles”. E. B. White, one of the
greatest novelists in American history, concluded, “I get
North Brooklin, Maine
impatient with the morning mail, because it is, in a sense,
May 7, 1961
my enemy—the thing that stands between me and a final
burst of creative effort.” Sound familiar? You can read
the entire letter, which is fascinating, in the sidebar. Dear Miss B.,
(Source: Letters of Note [website].) I’m sorry this letter has been put
off for so long, but there has
The problem is that email is endless. Some of it comes been serious illness in my family
from people with good intentions, and a lot of it comes and I have let things slide in
from robots or people who don’t give a damn. Every consequence.
email (good-intentioned or not) creates its own sense of I was surprised when my letter
urgency that, if humored, will seem more important than to Cathy Durham was returned
to me by you. Of the thousands
going to work, paying the bills, and (ridiculous as this
of letters I have written to
sounds) even building a LEGO set with your daughter. children, it’s the only one that
The more you engage in email, the more email engages has bounced, and I don’t feel
you. Put simply, there isn’t a simple solution to the email quite sure what happened. I
problem. Everybody has to make their own peace with it assume you were disinclined to
as best as they can. exhibit it, but I think the letter
belongs to Cathy and if you’ll
However, using the best tools, the automation your send me her address I’ll return it
—she might like to have it about

23
computer can provide you, and a little
common sense, you can make a bad
situation much more bearable. That is really
the point of this book: to confront email, to
help you make smart decisions about how to
deal with it, and to provide you the right
tools to pull it off.

It took that lost moment of not being able to

play with Sarah for me to realize I needed to
become the boss of email and not vice versa.
That is exactly what I’ve been doing for the
last year—studying, experimenting, and
developing new workflows that let me tame
the beast and even, once in a while, build
something really cool with my daughter.

24
 CHAPTER 2

TACTICAL
EMAIL
 SECTION 1

Getting Tactical

So how do you the tactical level.

conquer email? Whether you write email
There are two exclusively on your iPhone
levels to the with the stock mail app or
problem: tactical instead write email on your
and technical. On own custom mail application on
the technical level, your Mac, there are certain email
there are a lot of different techniques universal to all email systems.
tools, applications, and services to These tactical-level issues range from what
help you. This book is going to make you a to do with your inbox to how to handle
PhD on the technical side of email for your email signatures. This chapter will focus on
Mac, iPad, and iPhone. the best techniques for dealing with email
on this tactical level and gives you ideas you
But before we dive into the nitty-gritty, I’d
can use in any email program (even non-
like to spend some time looking at email on

26
Apple operating systems). This chapter is
going to discuss several principles of email
that I will be referring to throughout the
book. Where the rest of the book discusses
the how of email, this chapter explains the
why.

27
 SECTION 2

Your Inbox

YOUR INBOX IS NOT YOUR and keep it for later. (There is a

TASK LIST book on that: Paperless [iBooks
Store]).
Imagine that mailbox
outside your house. The one thing you are not
There is a pretty simple going to do is walk out to your
workflow involved with mailbox, look through your mail, and
paper mail. A very nice then stuff it all back in your mailbox,
postal worker (usually wishing the postal worker luck getting
they’re nice [YouTube]) tomorrow’s load into the already full
arrives at your abode and box. That would be crazy.
crams lots and lots of paper into a
little box. You then fetch the paper and Nevertheless, crazy is what a lot of us
sort through it. You throw some of it away. do every day. We look through our
You read some. You may even scan some inboxes at things we’re not exactly sure

28
what to do with, close the window, and go bankruptcy”. Many people will
back to Twitter or Facebook or whatever mindlessly delete great big piles
else helps us release our happy chemicals of important email with no
while we try to forget the piles and piles of actual plan in mind and then
electronic mail sitting there. immediately resume the
bad habits that got them
The next time we go back to our email
there in the first place. This
clients, we see the exact same emails we
is something like an
ignored last time plus a whole new pile of
alcoholic throwing out all
mail dropped there while we were away. At
the whisky only to head to
some point it becomes paralyzing.
the liquor store an hour
later. There is a better way.
EMAIL BANKRUPTCY
One solution is to add a secret email
So we struggle through this dysfunctional
address. Some people do this in effort to
relationship with our electronic mailbox
avoid a lot of the email noise. They set up a
until one day we open our email clients and
secret email address and only provide it to
feel as if we are getting sucked into a sarlacc
those nearest and dearest to their heart. The
pit (Wookieepedia). For a lot of people, this
problem is that inevitably this email address
leads them to simply delete the entire
gets distributed wider than you wanted and
contents of their inbox and declare “email

29
you’ve still got the overload problem on the PROCESSING YOUR INBOX
“public” email account.
Leaving all of your emails in your inbox
You can’t ignore that original account either makes as much sense as leaving all of your
because occasionally something comes in paper mail in the mailbox in front of your
and it is important to you, so now you’ve got house. You need to process your inbox. In
two accounts to deal with. Moreover, some 2007, my friend Merlin Mann gave a Google
friends will start sending you messages to Tech Talk about email called “Inbox
both accounts simultaneously and then all Zero” (website)(video). The talk is
hell breaks lose. You’re better off applying legendary among the geek community and
filters and using some of the other for good reason: it is dripping with good
techniques covered in this book and keeping common-sense advice about tackling your
just one email address. inbox.

If you’re reading this with an inbox count of There is a workflow that can help you avoid
four digits, you’re not alone. Don’t despair. email bankruptcy. With a little practice, you
Instead of declaring email bankruptcy, send can get really good at going to your mailbox
your existing emails to an archive (so you and leaving it empty. Here are the steps to
can at least search it later) and start fresh inbox bliss:
using the techniques from this book.

30
1. IF IT’S TRASH, TRASH IT. For instance, I may receive a
IMMEDIATELY. greeting card from a friend:

It is easy enough to trash offers “Dear Dave, I sure am glad

from Nigerian princes. you got that thing removed.
(However, with a good system You don’t look nearly as
for dealing with spam, covered hideous as you used to.
in Chapter 7, you shouldn’t need Cheers, Jimbo.”
to see email from Nigerian
The card may make me feel all
princes.) There are a lot of other
warm and squishy inside. It may
emails that may not seem as
even have a picture of a kitten
obvious trash can fodder but still
hanging from a branch on the
are. These are emails that you can
cover. Regardless, after a day or
see no possible reason for ever
two I’ll throw it away. However, I
needing again. Perhaps it is because we
have trouble trashing even the most
have these digital things in our lives and it
mundane email I receive from Jimbo (even
feels as if they have unlimited storage, but I
that one thanking me for feeding his pet
find myself much more resistant to trashing
gator Felix). Why is that? Maybe it is
email than I am to trashing similar paper
because emails don’t take up physical space
mail.
in our lives so we are more likely to keep

31
them. Nevertheless, they do take physical friends here. Almost everything I don’t
space on our computer storage devices. delete ends up in the Archive folder
Moreover, they take up room in the email eventually.
indexes our computers must track so they
Note that it is an Archive folder (singular),
can search out email for us. If the email
not Archive folders (plural). Back in the day
truly is trashable (even from a loved one),
I had lots of folders to hold old email. I had
trash it.
folders for friends and family. I had folders
for the day job. I had folders for every case I
2. IF IT’S ARCHIVAL, ARCHIVE IT. worked on. I had folders for emails from my
If Jimbo writes to tell me what a swell guy I favorite online news groups. You name it, I
am (some people think I am), I may decide had a folder for it. Before long my email
that is one worth keeping. Maybe I’ll want client had this long scrolling list of folders.
to read it the next time I need to buoy my
delicate sense of importance. That’s an email
requiring filing but no response. (What do
you say to someone telling you what a swell
guy you are?) Emails such as that go in the
Archive. On all of my email accounts, I’ve
got a mailbox labelled “Archive” where I
dump emails. I don’t just send emails from

32
Then I had to carefully click and drag each carefully creating, organizing, and filling
email to its appropriate folder. If I missed that detailed folder hierarchy is wasted.
and dropped the email in the wrong folder, I With modern email clients, you can dump it
had to go drilling to find it and put it in the all in one folder and you will find it. There
right place. I also found myself facing an are some exceptions to this rule, and I’m
existential crisis every time I had an email going to explain those further later in this
that could potentially fit in multiple folders. book, but the big point here is that the days
Does this email go in the Jimbo, Friends, or Gator of filing emails in particular folders are
folder? Because I was crazy, I probably largely over.
created a new folder called “My Friend
Jimbo’s Gator”. If that is you, stop the If you are reading these words and the
madness. Every email client in idea of using just one archive for your
this book has a remarkable email is sending cold chills down your
search engine. I’m going to teach spine, my advice would be to
you how to use them in later try it for a short time. You
chapters. With all of my email in a will probably find you spend
less time sorting mail and still can
single folder, by typing Jimbo and
find whatever you need.
gator in the search box, I can find
that same email with zero upfront Some people will create single year
investment of time labeling and filing. archives, like Archive 2013 and Archive
All of that time you are spending
33
2014. That way, they can move the archive
out of their email application at the end of
the year.

If you absolutely must have folders, try your

best to limit it to no more than ten. Give
yourself at least a fighting chance to not get
lost in the morass of mailbox folder
hierarchy.

34
3. IF YOU CAN RESPOND QUICKLY,
Date: November 12, 2013 10:05 AM
THEN RESPOND QUICKLY.
To: Jimbo

If the mail is not trash or immediate archive From: David

fodder, you’re going to respond to it. If it is Re: Gator Kebabs

a short email that you can respond to Dear Jimbo,

Umm … no.
without a lot of time or effort, do it right
xoxo, David
then and there.

There are a lot of emails you can respond to

Date: November 12, 2013 10:00 AM
quickly. Productivity nerds (because they
To: David
are productivity nerds) like to get
From: Jimbo
Re: Gator Kebabs
“scientifical” about this. Some say only
Hey Big Dav-o,
answer if you can do so in two minutes.
I was wondering if you’d like to spend Labor Day Others say five. I really don’t care. If you
with me on the swamp. I just got a new banjo and can respond quickly and get it out of your
my gator kebabs are to die for.
life, go for it. Then archive the original email
Your pal, Jimbo
and get back to whatever blows your hair
back.

35
4. IF YOU CAN’T RESPOND After lovingly responding to the emails in
QUICKLY, RESPOND LATER. the Action folder, you can send them to the
—wait for it—Archive folder.
If you don’t have time to respond or you
need to think about it more before sending a There is a trap that comes with using an
reply, put the email somewhere else where Action folder. If you are unable to routinely
you can find it and reply later. One of the empty that Action folder, you’ve just created
easiest ways to accomplish this is to create the same overstuffed inbox with a different
an Action folder. Over the course of your label. Once you start using an Action folder,
day (or two), you’ll collect emails in this make a promise to yourself that you’ll empty
folder and when you’ve got more time you it out every few days. If you find that
can go through the Action folder and doesn’t work for you, you’ll have to look at
respond. So when you read that email from some the other options outlined in this book
an old friend asking you to attend a such as server-side email filtering, deferred
screening of a documentary on pork rinds email, and other magic tricks you’ll master
and you are torn between the desire to see before finishing this book.
your friend and the certainty that just
watching a film on pork rinds will make you
ill, you can move the email to the Action
folder and deal with it later.

36
5. IF THE EMAIL REQUIRES EVEN time. Doing so will lead to you falling off the
LATER ACTION, SAVE IT FOR LATER. wagon, and before long you’ll have
hundreds of these emails piled up. These
Some email requires a response that takes emails create future tasks. It could be as
longer than the day or two you need to work simple as writing a reply or much more
through your Action folder. This may be an complex such as setting up a binary filing
email that by its nature can’t be answered system. The point is you shouldn’t be
that quickly (e.g., “Write me back in two managing that task by leaving the
weeks about the status of my email in your inbox. Instead,
kumquat plants.”) or create a task in a task
something that is going to application and then send
take more time than you the email into the archive.
have to dedicate in the next
few days (e.g., “Send me the There are several great Mac
status report once you’ve and iOS applications to pull
finished labelling all the this off. Apple’s Reminders
office supplies in binary and app is free and syncs with
reorganized them iCloud between your Mac,
numerically.”). These emails iPhone, and iPad. On your
shouldn’t sit in the inbox or Mac you can drag an email out of
Action folder for weeks at a Apple Mail and drop it in

37
Reminders to create a link so you can jump (website) for this purpose. Those aren’t the
right back to the message later. Then assign only options, but they are a good start. The
a future date to the reminder and you’re set. point is that you need a trusted system for
setting up tasks for future email responses
I use OmniFocus (iPhone App Store) (iPad
so you can get them out of your hair right
App Store) (Mac App Store) (website) to
now and get back to work.
keep track of tasks. (If you want to learn
about OmniFocus, check out my screencasts I walk through all of the steps of processing
[website].) Some people use Evernote my inbox in screencast 2.1.

Screencast 2.1 Clearing Out My Inbox

38
ADDING COMPLEXITY
Having just a few places to sort mail makes
a lot of sense, but sometimes it is not
enough. While this workflow is a great start,
it’s not the only (or necessarily best)
solution for everyone. At the end of the
book, I’m going to outline my personal
workflow in detail, and it includes a lot
more steps than this. Specifically, I am using
various bits of software and Internet mojo to
filter all incoming email into mailboxes
relating to the different facets of my life, and
I deal with those with different frequencies
according to their relative importance. I’ll
explain all the tools I use in this book and
my workflow in detail in chapter 10.

39
 SECTION 3

Email Notifications

At some point along The first thing we do, let’s kill the Ding. too much email, make
the way of email no sense whatsoever. It’s
software like having someone in
development, somebody had the idea of your house tap you on the shoulder every
adding a notification system to your time a commercial plays on the
email client. Because each and television. The Ding is evil.
every one of us is our own very Seriously.
special flower, we need to be
Stop and think about it for a
notified at the very moment
minute. Every time you get any
someone writes us. Maybe this
type of momentum going with
made sense back when we
your work or, even worse, at
received two or three emails a
play, that Ding goes off. What
day. Maybe. However,
is the result? A rebellious piece of
notification systems in this day
your brain disengages from
and age, where everybody gets way
40
whatever real work you are doing and thinks that it may be the
most important email in the world. Like some Pavlovian dog, How many email
you then pull your phone out of your pocket or switch windows interruptions? A lot.
on your Mac to your mail application to find out that you’ve
been made an unbelievable offer for Dr. Funkenstein’s Fancy
Hair Tonic. At that point, you’ve successfully enabled someone
creating spam on the other end of the planet to interrupt your
1,008
work or play. Here’s the corker: in five minutes it is going to per Week
happen again.

Now think about the number of times that can happen in a day.
By default on the Mac, Apple Mail checks your email every five 4,320
minutes. On your phone, push notifications will do it more
frequently, indeed with every new email. Let’s just stick with per Month
five minutes to be conservative. A notification every five minutes
means 12 interruptions an hour. Assuming that you are around
computers or cell phones 12 hours a day, that is 144
interruptions a day. It gets worse when you start thinking in
52,560
terms of weeks, months, and years. per Year
So the question becomes what possible benefit are you getting

41
out of notifications that you are willing to go to email, and discover that the email isn’t
allow your iThingies to interrupt you 52,560 from Apple but instead a dodgy person on
times per year? Moreover, if you do think it the far side of the world who has $2.5
is somehow worth it, how on earth do you million for me just as soon as I give him my
get anything done or enjoy credit card and Social Security
any downtime? I think it’s numbers.
madness and everybody
Email has the word mail in it for a
should turn it off.
reason. By definition, mail (and
Badges are the same. Who email) is a delayed form of
can avoid that mocking red communication. You write
circle telling you that now something down, you lick a stamp,
you have four unread and you send it off. While email is
messages? My trouble is my 7,842 the digital equivalent of that, it
imagination. I look at that works the same way. Once you
badge and I begin to think press the Send button, there
the answer to all of my problems might be in should be no expectation that the other
there. Maybe someone at Apple likes my person will immediately receive it and reply.
book so much they’ve decided to buy 100 There are other forms of communication for
million copies so they can ship it on every that (such as the telephone and, to a lesser
new iPad. Then I stop everything I’m doing, extent, text messaging). People that expect

42
you to immediately read and reply to their through the roof. What is wrong with
emails are wrong, and you should not adopt you? Don’t you understand technology?
your behavior to fit their neurosis.
(Sadly, the above exchange is barely
In my day job, I’m a lawyer. There are lots fictional.)
of lawyers who have an inflated sense of
I check my email once in the morning,
their own importance. Routinely, I get
sometimes at lunch, and always in the late
telephone calls from attorneys like this:
afternoon. That is enough. Over the years,
Other guy: Did you read my email? I’ve received phone calls from lawyers,
clients, and even judges all complaining that
Me: What email?
I didn’t receive and respond to their email
Other guy: That email I just sent you. within minutes of them sending it to me.
It’s so important. I can’t believe you Every time I have the same discussion,
didn’t read it. What is wrong with you? explaining I don’t check email 12 times an
You are a bad person. hour. Those people that care have figured
out that if they need an immediate response
Me: When did you send the email? from me, they can call me on the telephone.
Other guy: I sent it five minutes ago. You shouldn’t feel the need to immediately
I’ve been sitting here waiting for your respond to every email you receive. The
reply. My blood pressure is going Onion (website) agrees.

43
My advice is to immediately start turning off
notifications, badges, new mail sounds, and
everything else that can get between you
and your work (and play).

I can hear your thoughts at this moment:

That’s all fine and dandy for you, Mr. Fancy
Pants, but if my spouse/boss/clients/parents/
kids/stalkers email me, I need to know
immediately. I get that. I even have a few of
those types of people in my life, too. There
are ways to let those people through and
later I’m going to show you how to do that,
no matter what email system you use. The
point is, however, those people are the
exception, not the rule. That way when you
do get a notification, it truly means it is
something worth the interruption, not a
smoking deal on Viagra.

44
 SECTION 4

Writing Email

So far, I’ve covered the tactical part of The default write order starts out with you
receiving email. Now I want to look at selecting the recipient for your message,
writing email. There are a number of which makes enough sense, but then
practices you can adopt with the way you everything goes off the rails. Next, it wants
reply to email to make life easier for you and you to type in the subject line for a message
your correspondent. you haven’t written yet. Because you
haven’t written the message, there is a bit of
REPLY WRITE ORDER mental friction between us getting our
thoughts together and making a cogent
I’ve always had a gripe with email
subject line at that time, so we skip it or just
application developers concerning email
leave it with whatever the mail client added
replies. When you go to reply to an email,
(e.g., “re: re: re: re: re: That Thing”).
the tab order is all out of whack.
Next, the application wants you to write the
body of your message. Rarely does the

45
application even prompt you to add an The next thing you do is write the message.
attachment, which means about half the That’s the reason you started this whole
time you’ll forget to add an attachment. process. I have some very specific ideas
Because the default write order is all out of about how to write the message body with
whack, so are the messages we often send inline replies—and explain that later in this
using it. It makes a lot more sense to add chapter—but for now get into the habit of
attachments next and then write the body of writing the message body next. Also on the
the message before filling out the subject line subject of the message body, try and keep it
and sending. I’ve got an alternative write brief. Email is a problem for everyone and
order that makes a lot more sense. sending a 3,000-word screed when all you
really want is to borrow the industrial
1. Add Attachments
plunger isn’t very nice.
Don’t you hate getting an email making
3. Add a Sane Signature
reference to a nonexistent attachment?
Don’t you hate even worse when you send Email signatures should be simple and
an email making reference to an attachment smaller than the body of the message. There
you forgot to attach? is more on this later in this chapter.

2. Compose the Message Body

46
4. Write the Subject Line

Finally, after you’ve attached any necessary Write Order According to MacSparky
files and written everything else, make an
intelligent subject line.

5. Enter the Message Recipient and

Copies

Waiting until last to add the recipient

assures you’ll never suffer from premature
email sendation.

6. Proof and Send

Read the whole thing one last time and send

it off into the world.

47
EMAIL RECIPIENTS actually remember doing this in high
school.) People back then didn’t make the
That Cc in your mail
decision to Cc someone lightly because they
client stands for carbon

Cc
knew what a pain in the neck it was. The
copy, which itself is a
trouble with email carbon copies is that they
reference to the old days
are ridiculously easy to pull off. Type in
when a copy of a
another name in a Cc field. That’s it.
document or letter was
made with carbon paper. As a result, once people figure out the Cc
Anyway, the old folks would literally make a field, they go crazy with it. I get carbon
carbon copy and send it off to someone else copied on emails that I have no business
when it seemed appropriate. This isn’t a new reading. Sometimes they do it to cover their
problem. Thomas Jefferson even had a backsides. Other times they do it to show
system for copying his letters as he sent how smart they are. Nearly every time they
them out (website). do it, they take a little bit more of my time
and attention without a good reason. Be
Back in my day, we went past carbon paper
stingy with those carbon copies. Only Cc
to the mimeograph (Wikipedia) but it was
somebody who really needs to be in the loop
still a big deal. You had to get this really
and has something to add.
smelly fluid, type the letter on special paper,
and then roll the paper through a machine
like some Gutenberg-inspired artisan. (I

48
Another ugly side effect of carbon copy unwanted correspondence. (There is a way
abuse is the Reply All button. If you are to autodelete these strings with email rules,
trying to share information or schedule a covered later in chapter 4.) Stop the
meeting between several people, Reply All madness. Stay out of these self-
makes sense but otherwise, step away. So congratulatory email chains. If you want to
often I’ll get a message from someone copied send a note of congratulations back to your
to 20 other people announcing their dog got friend, reply to your friend directly. Do not
rid of its fleas, they just graduated at the top Reply All. That way your friend gets your
of their rehab class, or something else they note about what a unique and special
felt like telling everyone they knew. When I snowflake they really are, and you don’t
receive these notes from friends, I’m happy show up in 20 other people’s mailbox. Then
for them but I also groan inside because I set up your rule and punch eject.
know that within minutes, and continuing
for the next week, my inbox will be under
attack from Reply All replies. Other
recipients get the message and, either
through ignorance or in attempt to show
everyone else how clever they are, Reply All
with their pithy response, which eggs on
others in the group to reply to that and
before long my email is exploding with
49
On the subject of Reply All, treat that horse-sized
button like a loaded gun. Reply All has duck?” This

Bcc
resulted in more hurt feelings, firings, event, dubbed
lawsuits, divorces, and other forms of social the
disharmony than any other setting on your
computer. Every time your mouse hovers
over the Reply All button, your Spidey
“Replyallcalypse”, is legendary on the
senses should tingle and you should ask
Internet (website).
yourself, “Do I really want to reply? To all?”

A final, cautionary tale on Reply All. In

2012, a student at NYU was trying to
forward an email from the Bursar’s office to
his mom. He accidentally hit Reply All and
ended up sending that email to 39,979 NYU
students. The recipients, being college
students and grasping the potential for
anarchy, immediately began Replying All to
39,979 people with probing questions such The final subject of consideration is the Bcc
as “Can I borrow a pencil?” and “Would you (blind carbon copy) field. This also has long
rather fight 100 duck-sized horses, or one roots in the pre-computer world. If you

50
were sending a letter to Franklin and a discussion. You want to tell everyone that
secret copy to Eleanor, you’d blind carbon you just won a cow chip throwing contest.
copy Eleanor and Franklin would be none (Yes, they exist [website].) However, you
the wiser. You can do that now by putting want to be a a good Internet citizen and not
Eleanor’s email address in the Bcc field on give everyone on your mailing list the email
an email to Franklin. Eleanor will get a copy address of everyone else on your mailing
of the email and Franklin will never know. list. What to do? Blind carbon copy
As an example, when I send emails to the everyone on your list.
opposing attorney on a lawsuit, I always Bcc
When you send that email, the recipients
my client. That way the other attorney does
will only see your email address and theirs.
not get my client’s email address, and my
Not only does this protect your friends’
client knows what I’m up to. I think you can
email addresses from unwanted disclosure,
go too far with Bcc. At some point, secretly
it also prevents that carbon copy cataclysm I
blind carbon copying everyone just becomes
wrote about earlier.
spooky. Use it where appropriate, but don’t
get paranoid.

Another appropriate use of the Bcc field is

sending out a notice to a big group of people
while at the same time preserving their
privacy. Let’s go back to the carbon copy

51
SUBJECT LINES THAT MATTER
Request to Borrow Your Industrial Plunger
At some point, it
The Cost to Replace Your Plunger?
became okay to send

Re: an email with a

subject line that
looked something like
I think the hangup with subject lines has a
lot to do with the fact that every email client
prompts you to type a subject line before
your message. The trouble is we aren’t
this:
exactly sure what the subject line should

“Re: re: re: re: re: re: Question?” read until after we write the message so we
skip it and then never go back. (See the
When you are looking at a list of 50 emails,
previous section about write order.)
how does this help you? If you are going to
take the time to write me, why not take a This collective ethic that it is okay to send
few more seconds and help me out with a emails with lousy subject lines sucks. I’ve
discernible subject line? surely done it enough times myself, but it’s
time to stop this. If we are going to help
The best subject lines convey a short version
each other conquer email, we have to start
of the key points and questions posed, for
spending a few more seconds writing subject
example:
lines that make sense.

Confirming Lunch Tomorrow

52
There are some other commonly accepted simple and don’t use many. If
shortcuts to use in subject lines. EOM means you can effectively use EOM
end of message. For instance, you could and NNTR, you are already
send an email with a blank body and a way ahead of the pack.
subject line that reads, “Yes, I will buy your
This isn’t rocket
kumquats. EOM”. Then your recipient
science. Imagine you
knows the entire contents of your message
are on the other side of
without opening it.
that email and you’ve
NNTR is another popular shortcut that got another 200 emails
means no need to reply. An NNTR message alongside it. Also
could have a message body. NNTR tells the imagine that you have no idea what the
recipient they don’t need to continue the purpose of the correspondence is as it
lunacy by writing back with something arrives because the the subject lines look
inane. like they were typed by 10,000 monkeys
with 10,000 typewriters. Now look at your
There are others such as “Action”, “Time
subject line and decide whether or not it’s
Sensitive”, and “Low Priority”. There is,
good enough to convey the key information
however, a line with this stuff. If, for
to your recipient. Start doing this right now
example, you need a guide for these codes,
and your email correspondents will love you
you’ve gone over that line. Keep them
more than their first big fluffy teddy bear.

53
INLINE REPLIES the specific part of the letter we were
addressing.
Back when we all had quill pens and
parchment to communicate with each other, With email, both of those problems are
we had to do a lot of signposting in our solved. We reply to an email and the
correspondence. recipient can see the original text right in
your reply. Also, the original text is
An Old-Timey Letter somewhere in the reply so we don’t need to
restate the original subject. The question
Dear Sebastian, becomes how effectively we leverage these
I am in receipt of your letter dated August benefits.
1, 1776. In reference to your recent bout of
By default, every mail client I’ve ever used
hookworm infection, I recommend much
sets up top-posting replies. That means you
leeching and bleeding.
type the reply to an email with all of the text
Cordially, of the original message below it. This is not
Alexander ideal. Top-posting requires the recipient to
decide exactly what you are talking about,
which isn’t always easy.
Back then we had to tell the recipient (1)
which letter we were responding to and (2) Take, for instance, this email.

54
 As the reader you can imply that Wolfgang
Dear Wolfgang, agreed to the loan and forbad the medical
disclosure, but are you sure? The reason we
I know you’re busy but please give me a quick
do top-posting replies is because they appear
reply. Can I borrow $10,000 and is it okay if I tell
Thelma about that medical condition of yours?
easier. I’d argue they aren’t easier because in
order to send a top-posting reply correctly,
Sincerely, you have to go back to the old days and
Meriweather summarize the points you are replying to
(e.g., “In reply to your request for $10,000,
absolutely not.”). Also, I think we lean
toward top-posting replies because this is
what our email clients push us toward, and
Wolfgang gets the email and responds. that has always been the way we replied to
written correspondence. (It’s the only way to
Meriweather,
respond to written correspondence.) Top-
Yes and absolutely not.
posting is not the best way to reply to email.
Now we are using computers and we have
Wolfgang new and better options available to us. In
this case it is the inline reply.

55
Imagine taking a written letter, cutting it into pieces, glueing
A Sample Inline Reply
it on a piece of paper, and writing your replies to specific
questions below the relevant portions of the glued-on written Meriweather,
letter. Computers make this possible (and easy). These are
called inline replies. Inline replies remove the possibility of > I know you’re busy but please
misinterpretation. As the name implies, inline replies take > give me a quick reply. Can I
place right inside the text of the original message where you > borrow $10,000
leave the original email text and reply under the relevant
Absolutely not.
portions of the original message. Wolfgang’s inline reply is in
the sidebar.
> is it okay if I tell Thelma about
If you take the time to write inline replies, your > that medical condition of
>yours?
correspondent will always know exactly what you are talking
about. Unless I’m replying to a very simple email, I always do
Yes.
inline replies. The longer the email you are responding to, the
more sense this makes. With all of the email clients Sincerely,
recommended in this book, creating an inline reply is not Wolfgang
difficult. Start a reply and type your greeting at the top (e.g.,
To my deadbeat friend Meriweather). Then insert
carriage returns inside the source email text where you want
to reply. The end result is a very clear email that your

56
correspondents will appreciate. It takes a 2. PRUNE THE EMAIL THREAD.
few seconds more to create than a top-
posting reply (Seconds!) and makes your Nobody likes receiving an email that
reply much clearer to its recipient. includes a thread of 20 prior emails and
responses. Nobody is going to read it and
they won’t appreciate all the word noise you
BEST PRACTICES FOR EMAIL
are throwing their way. Prune old emails out
REPLIES of your reply. Most applications make it
There are some rules of thumb that make a relatively easy to select big chunks of text.
lot of sense for writing email replies: Rarely can I justify keeping more than two
or three prior emails when responding to a
1. RESPECT THE RECIPIENT’S TIME. thread. Delete everything you don’t need
and send a nice, concise, tight response.
Whoever is on the receiving end of the email
has no control over what you are about to
3. NO OPEN-ENDED QUESTIONS.
send. Respect the recipient’s time by
thinking through your response and writing Ask detailed questions enabling your
a tight, short email. Spending a little bit of recipient to give a detailed answer. “Do you
your time to save a lot of your recipient’s want the ball bearings made of unobtanium
time should be the rule. or dilithium?” Whenever you send an email
with an open-ended question at the end such

57
as “Thoughts?” or “Ideas?”, a puppy dies.
Please don’t kill puppies.

4. DON’T SHOUT!

DON’T YOU HATE IT WHEN

SOMEONE WRITES TO YOU IN ALL
CAPS? DOESN’T IT FEEL LIKE
SHOUTING? WHAT’S EVEN WORSE
IS WHEN THEY decide to selectively
leave portions of the email in lower case and
then GO ALL CAPS WITHOUT
WARNING TO EVEN FURTHER
CREATE THE SENSATION OF
GETTING YELLED AT.

I hate that.

58
EMAIL SIGNATURES McSweeney’s did an essay
on lawyers’ email signatures
Signatures are another
that is absolutely worth
opportunity to abuse your
clicking out of this book to
readers. As a lawyer, I
read (website). My favorite line explains,
frequently get emails from other lawyers
“This disclaimer is not unlike the ceaseless
where the signature block is larger than the
blaring of a distant car alarm—a once-
text they are sending me. In their signature,
sincere warning that has evolved into an
they will include paragraphs and paragraphs
unpleasant nuisance, rendered meaningless
of text about what to do if the email gets lost
by its own ubiquity.” Sometimes email
and explaining how important they are.
signature gibberish is required. For
They’ll even list their email address since,
instance, some people in the financial
apparently, I wouldn’t have the common
services industry are often required to do it.
sense to look at the top of the email if I
However, the vast majority of us are not
wanted to find their email address. Then
required to do so and shouldn’t.
they add two or three pretty graphics that I
don’t care anything about but may mislead Signatures should be as simple as possible.
me to think there are some attachments of Don’t add any fancy graphics that require
relevance, leaving me to click on them only the recipient to wonder if you’ve attached
to see a very lackluster law firm logo. something important or just an asinine logo,
and don’t go crazy with typography either. I

59
keep my signatures largely in plain text and like you spent more time crafting your
just a couple lines. My usual signature for signature than the response.
my lawyer job lists my name, my firm’s
I insert my email signatures, when I use
name, and my phone number. That’s it:
them, using TextExpander (website). There

David Sparks are several ways to build in email signatures

Finch & Sparks on the various Mac and iOS applications

123-456-7890 covered in this book and I will explain them
later. The point of this discussion is that you
I don’t use a canned signature for personal start thinking about using simple signatures
email correspondence. Instead, I usually that don’t subject you to ridicule.
write David. Rarely, I use an email signature
for my MacSparky correspondence that lists
my website and calls me an “author” and
“broadcaster”, which makes me feel really
cool. If I want to feel cryptic, I’ll just write
D.

The point is to keep it simple. Don’t add

graphics, and just give the key information
so when you send an email, it doesn’t look

60
AUTOMATED REPLIES
An Away Message with Too Much Information
A lot of email clients provide a system for
you to send automated replies. Usually Hello,
found in an email clients’ Settings tab under
vacation responders or vacation replies, this I am going to take a three-hour tour on a small
is often used for vacation messages. boat with a bizarre group of travelers, a
confused captain, and his scatter-brained first
mate. I shouldn’t be long. Unless the weather
starts getting rough and things go horribly
wrong, I’ll reply tomorrow.

In the meantime, you can contact Jenny at my

office at 123-867-5309.

Your pal,
The Prof.

The problem with the above sample is that it

gives way too much detail about what the
Prof. is doing. A professional work message

61
simply says you are “away” or “out of town”. CONSIDER THE NECESSITY OF
I’m not against away messages; they give REPLY
immediate feedback to the correspondent
A lot of email doesn’t need a reply. If
and let them know when you’ll be back.
someone writes you,“Thanks”, leave it at
I’ve also seen some people use that. Don’t write back, “Thanks for saying
autoresponders to broadcast the general thanks.” That just embarrasses everyone
status of their life. It will say they are very involved. “Great” and “Awesome” are also
busy and they typically don’t answer email frequent offenders. Any time you find
for at least a week. “Hey everybody. I suck yourself writing a one or two word email
and it takes me 6.2 weeks to answer email. that isn’t “Yes” or “No”, ask yourself if it is
Peace out.” On one hand, I see this as really really necessary.
responsible way to communicate
expectations. On the other, it always leaves MOVING FORWARD
me feeling a bit put off when these messages
With all of these tactical concepts in mind,
bounce back at me. Maybe it is because I
let’s now roll up our sleeves and dive into
don’t get offended when people take a long
the technical side of email. Put simply, it’s
time to respond to me in the first place.
time for you to become the boss of your
email.

62
 CHAPTER 3

HOW EMAIL
WORKS
 SECTION 1

Why You Should Read This Chapter

Email, by its critical as an email power user because this

nature, requires simultaneously explains some of emails’
the Internet. As limitations and provides us users a vector to
users, it is easy to game the system and get better at email. So
lose sight of this. as much as you want to skip this chapter—
We think of email as don’t. Not only are you about to learn how
a thing that is on email works, I’m going to point you to some
our computers or on services that take advantage of email
our phones but in technologies that will change your game. So
reality our phones, let’s stop for a moment to talk about
tablets, and computers underlying email technologies and how the
more likely only have an image of that email Internet robots think about your email.
that actually exists somewhere out there on
the Internet. Understanding this fact is

64
 SECTION 2

Email Protocols

POP MAIL more than one computer, and

POP
this was reflected in the basic
For the Internet pioneers,
POP architecture.
figuring out how to send mail
using a computer was actually POP, in essence, is a dummy
pretty tricky and, of course, one-way connection from a mail
everyone did not agree on the server to your computer. A POP mail server
best way to go about it. One of the first gets a new mail message from somewhere
standards for handling email was the Post else on the Internet and waits for you to log
Office Protocol (POP)(Wikipedia). POP in. When you do, the POP sender licks the
was born in 1984. Think about it for a virtual envelope and pushes the email down
moment. Ronald Reagan was the U.S. to your computer, emptying its virtual
president, The Terminator was a new movie, mailbag into your computer. The email then
and the POP email premiered. Back in those resides on your computer for you to read,
days, it was unlikely a person would have process, and store. In a lot of ways, the POP

65
email protocol is the most similar to the way person. The message is received, then the
paper mail is delivered in the physical message is delivered. (I know this is a
world. The Internet is a virtual delivery simplification, but stay with me.)

Screencast 3.1 How POP Email Works

66
For a lot of people POP mail worked just as the server was concerned, it handled that
fine for a long time. Things, however, got email when it was delivered to your desktop
more complicated when people began using Mac, and the server was done with it.
more than one computer to read email. This
This made computer users a little crazy. So
was initially a problem for corporate types
in response, network administrators flipped
who had a computer on their desk and a
a switch on the POP servers that kept the
laptop for the road. The problem began
original email message on the POP server.
spreading to everyone else with the arrival
So, returning to the analogy, the mailperson
of smartphones, cheap laptops, and other
put a copy of the mail in your inbox and
connected devices. Suddenly, the issues
kept the original. This way, when you
inherent in POP’s delivery system became
logged on with your phone or laptop, the
obvious to everyone.
message was still on the server and was
Put simply, we all had more than one delivered again. The problem is that the
mailbox. POP would deliver a message to virtual POP mailperson wasn’t very smart
our desktop Mac mailbox, emptying its and he would not remember he already
virtual mailbag, and when we logged on delivered the message once or even know
with our laptops and phones looking for that what you did with it.
important email we knew we saw on the
This “fix” created its own set of problems.
desktop computer, the POP delivery robot
Because the POP standard was always
said, “Sorry. Nothing here. Empty.” As far

67
intended to be unidirectional in its mail more. Most email service providers have
delivery, the server had no idea what you moved on. The only places I routinely find
did with that message after it was delivered. POP mail services today are those free
So if you first received the message on your accounts you get from Internet Service
Mac and filed or deleted it, the server had Providers (ISPs). Cable companies, for
no idea. The next time you logged in with instance, still often give their users POP
your laptop, the exact same messages mail accounts.
arrived in your inbox all over again. Users
The answer to all the problems POP mail
found themselves deleting the same spam
creates is a different email standard that can
email multiple times. They also had to file
talk back and forth between the server and
email multiple times and, of course, in no
your email clients, so when you delete or file
time at all they had different versions of
a message on one computer, it happens
their email library on each of their
everywhere else. Enter IMAP.
computers and hijinks ensued. If this story
sounds familiar to you, you’re probably
using a POP mail service.

POP mail used to be the standard. Most

people had a POP mail account and one
computer, and they were blissfully ignorant
of POP mail’s failings. That’s not so true any

68
IMAP MAIL in the bill drawer, so does he.

IMAP
Creepy, right? IMAP talks
There’s actually some dispute
with your mail applications
over exactly what IMAP
and keeps track of what is
stands for. The acronym is
going on with your mail.
most commonly used to stand
Indeed, what is really
for Internet Message Access
happening with IMAP is your email never
Protocol so let’s stick with that. IMAP
leaves the server and those local emails on
(Wikipedia) introduces two-way
your phones, iPads, and Macs are just
communication to the mix, allowing your
mirroring the IMAP mail. The truth, as they
mail server and the mail client on your
say, is in the cloud. When you delete a piece
computer/tablet/phone to talk to one
of spam mail on your computer, the IMAP
another. IMAP, which first appeared in
server takes note and deletes the spam mail
1988, is no late bloomer in the email services
on your server. Then when your iPhone
game.
later checks in, the server says, “Hey, I’ve
Returning to the real world analogy, deleted that spam message,” to which your
imagine IMAP as a creepy mailperson. He iPhone responds with the digital equivalent
delivers your mail and keeps a copy of of “okey-dokey” and deletes the same
everything he delivers. He then peeks message from its inbox. This way, your mail
through your window and if you throw is always in sync everywhere. As a result,
away junk mail, so does he. If you put a bill IMAP always knows what emails you’ve
69
 Screencast 3.2 How IMAP Email Works

read, replied to, filed, and otherwise dealt it will already appear as read when you
with and shares that information with every open your mail application on your iPad.
connected email device. When you open that
IMAP also tracks and syncs email folders.
letter on your Mac from your second cousin
When you create a folder on your Mac or
asking for money to buy a new sump pump,
iPad, it populates up to the server and then
down to your other devices. Have you ever

70
created a folder on your Mac to see it later One of my favorite geeky little pleasures is
magically appear on your iPhone? If so, you watching my email client send off 42 emails
probably have an IMAP server. These after landing from a long flight. I imagine
synced folders make it possible to use many these little folded electronic paper airplanes
of the tricks, such as use of the Action and firing off in all directions to my
Archive folders, covered in the Tactical correspondents all over the world like
Email chapter. something out of Harry Potter and it makes
me happy. (I am such a nerd.)
Just because IMAP is a server-based
solution doesn’t mean you don’t have local POP mail has some advantages. It doesn’t
copies of your emails. All of my Macs have use as much bandwidth (since it only talks
copies of all of my email. My iOS devices one way) and if you are freaked out about
don’t have all of my email because they don’t the way IMAP keeps your messages on a
have adequate space to hold it all but they server out there somewhere, POP lets you
do have my most recent email stored locally. download all email to your computer to
Regardless, because I’ve got local copies, satisfy that growing sense of paranoia. In
email largely works even when I’m off the my opinion, however, these advantages are
Internet. The next time I connect to the greatly outweighed by the monumental pain
IMAP server, it checks all the offline in the neck that comes with a POP account
activity and syncs everything up, including if you own more than one Internet-
sending held messages from my outbox. connected thing.

71
Many of today’s current email services are IMAP, it really isn’t IMAP. (I’m going to
based on IMAP. The Internet is full of explain Gmail next.) Also, except for a few
companies that will, for a fee, sell you an apps designed specifically around Gmail,
IMAP-based email account. (I pay for I’m not aware of any currently developed
IMAP email on my MacSparky.com domain mail application that does not support
from Hover.com [website].) Apple’s iCloud IMAP mail.
mail and Yahoo mail are also IMAP mail
One of the advantages of an IMAP mail
services. Unfortunately, not all IMAP
service is that because the mail is stored on a
service providers use the same
server, you can offload some of the work of
implementation of IMAP. After all, the
sorting and organizing that email to Internet
standard has been around since 1988, and
robots. In the last few years, we’ve seen
there are a quite a few iterations lying
some very sophisticated services that will
about. Quite often, this is another instance
predictively organize your email into folders
of getting what you pay for. The free IMAP
for you. There are two that I think are
you get from an ISP is usually a lot rougher
worthy of recommendation: Sanebox and
around the edges than one you pay for.
AwayFind. I rely on these services to avoid
Personally, I’ve been happy with Hover’s
E. B. White’s despair and will be explaining
implementation and use that for my
them at length later in this chapter.
MacSparky accounts. Another IMAP
service provider worth checking out is
FastMail (website). While Gmail supports
72
GMAIL lot of times it actually is a good thing. You
can go overboard with it, though. Adding
Gmail is an outlier in all
labels to emails takes time. If you deal with
of this. Gmail supports
a lot of email, that time stacks up pretty
both POP and IMAP
quickly.
protocols, but at the
same time Gmail is The big takeaway for Gmail (at least with
neither POP nor IMAP. respect to discussing the underlying
Gmail organizes email with tags technologies) is that because it really isn’t
(called labels). You can place multiple labels POP or IMAP, traditional mail applications
on a single email letting you organize by sometimes have fits dealing with Gmail.
several criteria. For example, I could label Some clients deal with multiple labels on
an email “Eddie Smith”, “friend”, “plunger”, Gmail by making multiple copies of the
and “money owed”. I could then search for message and creating a separate folder for
all emails that contain the labels “friend” each tag. Crazy. If you use Gmail a lot, I’m
and “money owed” and this email would going to recommend you use Gmail’s own
appear. Using IMAP, you can’t place an web interface or one of the applications built
email in more than one folder so there is exclusively for managing Gmail. Gmail gets
only really one dimension of organization. its own chapter in this book, chapter 5, so
Labels give you as many dimensions as you you’ll get all the nitty-gritty soon enough.
please. That seems like a good thing, and a

73
 I CLOUD EMAIL devices such as Android phones and
Windows computers.
iCloud (website) is the
name Apple applies to As IMAP mail services go, iCloud is pretty
a whole bunch of good. For the last few years Apple has been
different web and investing heavily in server farms, and
cloud-based services. iCloud Mail is becoming increasingly
One of those is iCloud reliable. Because it is an Apple product, it is
mail. iCloud accounts are free when you buy tightly integrated in the OS X for Mac and
an Apple device, but as you use iCloud iOS operating systems and is easy to set up.
more, you may need to buy additional
storage from Apple. In addition to specific email clients, you can
access your iCloud email account from any
For the purposes of this book, I’m just going web browser at iCloud.com. Apple’s web
to to talk about iCloud Mail, which is portal to email is remarkably Apple. It
Apple’s version of an IMAP mail service. doesn’t have the utilitarian look (or amazing
You don’t have to use Apple’s mail client to keyboard shortcuts) you get with Gmail, but
access iCloud Mail. It works on any email it looks great and has a lot of nice little
client that supports IMAP, which is pretty touches that make it feel more like an
much all of them. You could even access and independent application than a web page.
use your iCloud email account on non-Apple

74
 Gallery 3.1
Gallery 3.1 shows to an email of
email management your choice.
at iCloud.com. These rules are
applied on the
iCloud also has
iCloud.com
the ability to
servers so the
apply server-side
emails get
rules. I’m going to
managed even if
explain email
all of your
rules in depth
computers and
later in this book
mobile devices are
in chapter 4.
turned off. (This
Email rules let Start by logging in at iCloud.com is in contrast to
you automatically
the Apple Mail
perform actions
application rules
on email matching
that are much
certain criteria.
more robust but
iCloud.com’s implementation lets you look
also require a running Mac, which is also
for emails with particular senders,
covered in Chapter 4.)
recipients, or subject matters and trashes or
files those emails for you, or forwards them

75
Recently, Apple has come under criticism
about the way the iCloud Mail services filter
spam. Specifically, Apple can sometimes get
too aggressive with spam filtering and
messages that should be delivered aren’t
getting delivered. In 2013, Macworld
magazine explained this in an article
(website) where the authors, by including
the term “barely legal teens”, were unable to
get messages to one another even though
they were not the kinds of messages those
words imply.

I’ve been using the Apple Mail service for

years for my personal account and I’ve been
happy with it. Since I spend so much time
working on Apple devices, having an iCloud
email account is really convenient.

76
MICROSOFT solutions. That is no longer true.
EXCHANGE Now OS X for Mac and iOS
both natively support Microsoft
Microsoft has its own mail
Exchange. Indeed, in my
and messaging protocol for
experience my iPad and iPhone
Microsoft Exchange.
support Microsoft Exchange
Exchange is one of the most
better than the Windows 7
common solutions for
computer sitting sadly in the
syncing up mail, contacts,
corner of my office. You can
calendars, and tasks in
easily access Microsoft
companies. The mail
Exchange with the native Apple Mail
component works a lot like IMAP but also
clients. Microsoft also has a version of its
differs with respect to the specifics. While I
email/calendar/contact/task application,
know lots of people who use Microsoft
Outlook for the Mac, which is covered in
Exchange technologies at their work
chapter 6.
(indeed, I use it at my day job), I don’t
know anyone that uses it for their personal
account.

For a long time, Microsoft Exchange email

meant you were limited on your options for
accessing your email to Microsoft-specific
77
THE CASE FOR OWNING YOUR Apple’s iCloud Mail. Those accounts aren’t
OWN EMAIL DOMAIN dependent on where you live or who you
pay for that copper wire leading into your
While on the topic of email technologies, I’d
secret lair. However, some emails can feel
urge you to consider the idea of owning
like a stigma. When I see someone with an
your own email address. So often, people’s
AOL address, for instance, I don’t expect
email is based on their Internet Service
them to be very computer savvy.
Provider (ISP) (e.g., hotmess@cableco.net).
I get why people start these emails: they are If you really want to do this right, take the
easy and free. However, these ISP emails extra step of setting your email to your own
are usually the worst when it comes to domain. It is not that expensive to buy a
service. They also often default to the POP domain, such as
standard, and they are not mobile. If you FirstName@LastName.com. Then you
pack up and move to a different town with a could set up an email at your own domain,
different cable or DSL provider, you’ve got such as atticus@finch.com. That way you’ve
to get a new lousy free email account and got an email address that truly is yours—for
get word out to your friends and family that life. To register a domain costs about $10
the old one no longer works. per year. You’ll also need to get an email
hosting service, which is offered by many
It makes a lot more sense to set up your own
domain name server companies.
portable email. You could do this with an
email provider such as Google’s Gmail or
78
When my daughters were born I
immediately registered their domains. Now
they are teenagers and the domains are still
parked but I’m sure they’ll want them at
some point. The nice thing about owning
your own email through your own domain is
that it is uniquely you and lets you avoid
hitching your email address to someone
else’s product.

79
 SECTION 3

Common Email Account Settings

No matter what email vendor you use, there EMAIL PASSWORD

is a good chance that at some point you’re
Make sure to keep your email password
going to need your account details to set up
somewhere safe. A spreadsheet document on
an email client or troubleshoot a problem.
your desktop labelled “Passwords” is not
Here’s the skinny.
safe. I use 1Password (iOS App Store)
(Mac App Store) (website). There are other
EMAIL ADDRESS options depending on which platform you’re
I’m a big fan of simple email addresses. on. I write a lot more about email passwords
Mine is david@macsparky.com. Email in chapter 8.
addresses such as chugsalot@domain.com
and LoveFluffyCats@domain.net seem like a
great idea right up until that point you need
to give your email to a prospective employer
or new client. Keep it simple.

80
FULL NAME email address (e.g., david@macsparky.com)
but sometimes it’s the name without the
Use your full name. For example, David
email address (e.g., david). A few years ago
Sparks, or better yet, Sir Pincus Redbottum
it was the username on the account (which
III, Esq.
might be something such as davids42148)
with the mail server when you signed up for
DESCRIPTION the service and not your email name. This
When setting up an email account in your practice led to much rending of garments
email client, you’re often asked for an and, as far as I can tell, none of the major
account description. If you have multiple email providers do this anymore. If your
accounts, this helps keep your head on mail service doesn’t provide you any
straight. For example, you could describe guidance, start with the email address.
your Microsoft Exchange account as That’s usually the answer.
“Work” and your iCloud account as
“Home”. INCOMING MAIL SERVER
This is the mail server that throws email at
USERNAME you. Usually it is very simple, such as
Often account setup will prompt for a mail.hover.com or imap.mailserver.com. If
username. This is the name attached to the you’re feeling lucky, try using mail or imap
user on the mail server. It is usually your along with the name of your server (e.g.,

81
 1Password’s Email Settings Screen
mailserver.com). If that identical server. Others
doesn’t work, do an use a slightly different
Internet search with server, such as
something such as “mail smtp.mailserver.com.
settings for [insert (SMTP stands for
service] mail account” Simple Mail Transfer
and you’ll find what you Protocol.) Again, a web
need pretty quickly. The search or call to your
mail server settings mail server’s customer
always throw people off. support should set you
Once you figure it out, right. Several of the
write it down better mail server
somewhere. (This is companies even have
another thing I do in step-by-step screenshots
1Password.) showing you how to
enter these credentials
OUTGOING MAIL with all of the major
SERVER email clients.

This is like the incoming mail server.

Indeed, with some services they use the

82
SSL coffee shop’s wireless router in that
transparent envelope. It didn’t take long for
When the IMAP and POP protocols were
crooks to figure this out, and now there will
first created, nobody thought much about
routinely be some reprobate in the corner
security. Moreover, nobody was thinking
monitoring the traffic, looking for someone
about things such as WiFi and wireless
broadcasting their email “in the
communications. As a result, they didn’t
clear” (which is nerd speak for
build any encryption into email. When you
unencrypted). Once they get your email
sent an email message, it was wide open for
username and password, then they log into
anyone to read as it made its way through
your email and all hell breaks loose. Don’t
the Internet. It was like sending letters with
believe me? Think about all the emails you
transparent envelopes.
have with account details, credit card
This problem was mitigated by the Internet transactions, banking information, and other
Service Providers that have been details of your life you’d rather keep on the
systematically upgrading the security of down-low. The concept freaks me out so
your data once you put it in their hands. The much that I almost always prefer to use the
real trouble started with WiFi. When you go Internet connection from my iPhone or iPad
to the coffee shop and suck down your triple even when there is free WiFi.
shot latte while answering email, you are
SSL (Secure Sockets Layer) is a bit of
sending mail, usernames, and sometimes
magic that encrypts that data over the air so
even passwords from your computer to the

83
nobody else can see it. You’ll see this on
POP IMAP SMTP
your banking and other e-commerce sites. It
Standard 110 143 25 or 2525
also works on your email and you should
Secured 995 993 465
always turn it on. It is a method by which
your normal “in the clear” information is (SMTP is a separate email protocol used for
wrapped up inside an encrypted envelope. moving email around the Internet.)
SSL is employed on the web to secure e-
commerce and banking websites, and it does The point here is that if you are prompted
much the same for your email. for a port, the above should work. If they
don’t, contact your email provider for the
details.
PORTS

Sometimes email configurations will ask you

to list a port. This is not making reference to
Portuguese wine but something more akin
to a shipping port with berths for all the
incoming and outgoing Internet data. A few
ports were set aside for email. These are the
most commonly used email ports:

84
 SECTION 4

Third-Party Mail Services

A common theme emerging another involves convenience. It

through this discussion is that is so convenient having your
all modern email protocols email sync everywhere. It
involve keeping a copy of your didn’t take long for people to
emails at Google, Microsoft, start thinking about the fact that if
iCloud, or some other server. their email was in the cloud, perhaps the
There are a few implications to cloud could manage their email for them
this. One involves security and privacy, while they were busy doing other things,
which is explained later in chapter 8, but such as building LEGO sets with their

85
children. A couple of respond to? Which were
noteworthy services doing filed? Which were
this are SaneBox and immediately deleted? You
AwayFind. can also have SaneBox look
at your Twitter, Facebook,
SANEBOX and LinkedIn contacts so
that it has a better idea of
SaneBox (website) is a
who is important to you.
service that monitors your
SaneBox does not read the
email accounts. It works
contents of your email.
with IMAP, Gmail, and
Instead SaneBox looks at the
even Microsoft Exchange
message headers, the
accounts. SaneBox will
senders, dates, and what you
monitor your email account and act on your
did with it. Nobody (and no computer) at
email for you. I like to think of it as my own
SaneBox reads your mail. This point was so
personal email robot ready to do battle with
important to me that I called and asked
all of those other email robots out there
before signing up. SaneBox then uses that
trying to take my precious time. This is a
information about what you did with your
fee-based service. When you first sign up,
email in the past to help automate what
SaneBox looks through your email to see
SaneBox will do with your email in the
what you did with it: Which emails did you
future.
86
EMAIL FILTERING SaneBox has picked up my instruction here
and normally puts those types of email
SaneBox’s banner feature is email filtering. messages in the News folder. The advantage
Specifically, it analyzes each new email of this is that I can deal with critical email
based on your past interactions with your from my email inbox, put off less critical
inbox. It leaves the most important messages mail in the Later folder until I have more
in your inbox and moves all others out into time, and decide—much later—if I’ll go
folders you create with your SaneBox through the News folder or delete it in bulk.
account. SaneBox also sends me an email (I
For example, I have several SaneBox appreciate the irony here) that summarizes
folders on my MacSparky.com email everything it sorted for me so I can make
account. One is called “Later”. SaneBox sure it is not screwing up. If it does make a
puts emails in the Later mailbox that are not mistake, such as putting an important email
from key people in my life. When I look at in the Later folder, I can manually move it
my email in the morning, the MacSparky back to the inbox, and SaneBox will notice
account may have two or three messages in and self-correct next time.
the inbox and the Later folder may have 20 SaneBox’s ability to determine the
or 30. I’ve also got a SaneBox folder on that appropriate folder for an incoming email is
account called “News”, in which I’ve pushed uncanny. SaneBox does a fantastic job of
marketing and newsletter-type emails. Again predicting where I want an email to go and

87
putting it there. Within a few days of email. It does, however, have your email
signing up for the service, I quickly began to login and password, which is required to
rely upon it. When it does make a mistake observe what you’re doing with your email.
and I move an email from the one SaneBox I spoke with representatives from SaneBox
to another, SaneBox remembers that the about this and they explained that the email
next time I receive an email from that access data is on a nonpublic server and
person. I was so impressed with SaneBox held very securely. They further explained
that I called and asked how they did it. They that their employees don’t have access to
explained that their servers aren’t just your email.
looking at whom the email comes from but
At the end of the day, to get a service this
also how I respond. An email that I open
useful you’re going to have to give the
immediately implies more priority than one
server email access. There simply is no other
that I don’t. Emails that I respond to are
way. This is one of those convenience versus
more important than emails I delete. There
security questions that each person has to
is a lot to how SaneBox works.
answer for themselves. In my case, I decided
A legitimate concern about using services to use SaneBox for my personal and
such as SaneBox is the protection of your MacSparky accounts but don’t use it with
email privacy. In order to work, SaneBox my day job lawyer account.
needs to have access to your inbox.
SaneBox never looks at the body of your

88
Regardless, this service really works and is your email database, this gives you an easy
tremendously helpful in separating the place to find all received email attachments.
wheat from the chaff. Think about this for
moment: How much would you pay THE BLACK HOLE
someone to check mail 24/7 and perform
this initial sort for you? It’s like magic. This One of the stock SaneBox folders is
alone is worth the price of admission for ominously named SaneBlackHole. I explain
SaneBox and there are additional features. later in chapter 7 why spam is such a
problem and why unsubscribing doesn’t
always work. Indeed, in some cases
CLOUD ATTACHMENTS
unsubscribing merely confirms that there is
Another common email gripe is the way a human at your email address and the
attachment files clog up your email crooks then send even more spam. If you
database. SaneBox attempts to solve this by drop an email into the SaneBlackHole
letting you attach your email account to folder, SaneBox will monitor all future
your Dropbox (website), Box (website), or emails and capture anything similar in the
IBM SmartCloud (website) and future. It is a user-controlled unsubscribe
automatically routing your incoming email button. This doesn’t just work for people
attachments to your cloud storage. In selling you Viagra either. There are some
addition to helping keep down the size of people in my life that have earned their way
into the Black Hole.

89
EMAIL REMINDERS and then pass the potato back over to them.
A challenge for you is to then remember to
A lot of times email exchanges are like a check back on the project later if they don’t
game of hot potato. Somebody may ask you respond. SaneBox allows you to add
to do something on a project. You’ll do it reminders to outgoing email.

Screencast 3.3 Configuring and Using SaneBox

90
If you send an email to your coworker and folders will disappear from your inbox until
copy (or blind copy) the email to the designated time. You can also set up a
1week@sanebox.com, in one week SaneBox custom folder with a different defer date.
will throw the email back at you (unless you While I was initially skeptical about the
have received a response from that person). wisdom of deferring email, I’ve come around
It is all really clever. It doesn’t just have to to appreciate it as I wrote this book. There
be one week. It could also be is some email that can wait until tomorrow,
2days@sanebox.com or or Saturday, or next week and getting it off
10minutes@sanebox.com. your plate by deferring it is a good way to
make that happen.
Instead of replying to your coworker you
could also forward the email to If you are dealing with a large volume of
1week@sanebox.com and then SaneBox will email, SaneBox can be some of the best
resend you the email at that time. money you spend to help manage the
onslaught for you. I will explain my
DEFERRING EMAIL personal email workflow at the end of this
book in chapter 10 but for now I can tell
SaneBox has a mechanism for deferring you SaneBox is a critical component to that.
email through mail folders. By default it has
@SaneTomorrow and @SaneNextWeek
folders. Any email you copy into those

91
Can you tell I’m pretty smitten with
SaneBox? Screencast 3.3 explains some of
SaneBox’s best features.

92
AWAYFIND to someone’s email within
minutes, it will recommend
AwayFind (website)
adding them to the list.
attempts to settle the
problem of email AwayFind will also look for
notifications. I have already emails on a particular topic.
explained my disdain for email notifications. You create these by providing AwayFind
Nevertheless, there are some people for keywords that you want it to look for. For
whom you will want notifications. Perhaps instance, if you add the words sales proposal
you have a boss that expects you to reply to to an AwayFind search, any email matching
emails within 10 minutes or a client project that criterion will give you an alert.
for which you absolutely must know as soon
as an email arrives. Rather than constantly One of the most clever implementations is
checking your email for these key people or the ability to look at your calendar and
events, AwayFind checks your email for you notify you if that person emails you. For
and notifies you when you receive an email instance, if I’m going to meet Brett in the
from a specific person or concerning a next hour and he sends me an email,
specific subject. AwayFind will send me a notification
regardless of whether I designated him as a
AwayFind even looks at your email history person to follow.
to help you decide which people are
important to you. If you routinely respond

93
There are several methods for AwayFind to notify you. The AwayFind iPhone App
You can receive a text message or be notified through
the AwayFind iOS App on your iPhone (iOS App
Store). AwayFind is a paid service, though a free plan is
available.

In my experience, AwayFind works best with Gmail

and a Google Apps account. The Gmail integration is
great, and many of the AwayFind features and services
will appear right in your Gmail window. Apple now has
a similar service with VIPs (covered in chapter 4), but
they are not as smart as AwayFind. VIPs focus on
people and not on subject matters or upcoming
appointments. Also, you can’t set VIPs to auto-
terminate like AwayFind can.

Now that you’ve wrapped your head around how email

works, let’s put this to practice with some of the most
popular mail applications and services available for the
Mac, iPad, and iPhone, starting with Apple Mail.

94
 CHAPTER 4

APPLE MAIL
 SECTION 1

Apple Mail

For the longest time, the Mac, it was Apple’s

there was a real shooting Mail application (or app),
war between rival email and for Windows, it was
client applications. Microsoft’s Outlook
Several companies Express. When consumers
actively developed email started getting email
software and, as clients with their operating
customers, we had many systems that met most of
options to choose from. their needs, they were
That ended when the much less likely to shell
companies that shipped out money for an
the operating systems independently developed
started to include their email client. While this
own email clients. For appears to be changing

96
(and I’m covering some competing mail operating system in ways that competing
applications in chapter 6), Apple Mail is still clients simply can’t match. So let’s dig in and
the most frequently used mail client on the I’ll show you how to get the most from
Mac, iPhone, and iPad. Apple Mail.

In my first draft of this book I equated

Apple Mail to vanilla ice cream. In later
drafts, I explained how recent updates
added chocolate chips. However, as I finish
this book, it occurs to me that Apple Mail
has become quite powerful including
specialized tools, keyboard shortcuts,
automation, and multi-platform features
(like VIP) that most email clients can’t
touch. We’ve come a long way from vanilla
ice cream. I am an email power user and I
use Apple Mail every day. On the Mac side,
Apple Mail plays nicely with third-party
plug-ins, which can dramatically improve
Apple Mail’s functionality. Also, because it
is Apple’s Mail application, it is tied into the

97
APPLE MAIL OVERVIEW increase its functionality. Also, the Mac
doesn’t use the same one-app-at-a-time
Apple Mail seeks to provide the user a
paradigm that the iPad and iPhone do,
common features set and email paradigm
making it easier to share data out of Apple
across all Apple devices. If you use Macs,
Mail on the Mac.
iPads, and iPhones, this is convenient. Some
of the features covered in this chapter just The iPad version of Apple Mail loses the
work across all of these platforms and can be plug-in support and keyboard shortcuts that
a useful tool in your arsenal. There are, come with Apple Mail but still does a good
however, differences between the platforms. job of presenting a lot of data regarding
your email. I often process email on my
The Mac version provides the most
iPad. I find the Retina display, onscreen
traditional email experience. It takes
keyboard, and easy portability to be the
advantage of your computer screen to show
right fit to let me manage email just about
you the most data. It also takes advantage of
anywhere.
Mac’s keyboard and mouse to include some
useful user interface mechanisms, such as The iPhone version of Apple Mail is, in my
keyboard shortcuts, to help you make quick mind, all about processing my inbox. Much
work of your email. Another advantage of of the Apple Mail user interface on the
Apple Mail on the Mac is support for iPhone is designed around reading, filing,
AppleScript (the Mac’s scripting language) and quickly responding to email on your
and the ability to add plug-ins to further

98
phone. I find the iPhone works great for
clearing out an inbox, but it’s not my first
choice for writing email of any significant
length. That’s me. I know people who are
comfortable writing long passages with the
iPhone keyboard. For them the iPhone is
where they manage most of their email.

The point is every iteration of Apple Mail is

a little different, and Apple Mail attempts to
take advantage of the platform it was
designed for.

99
 SECTION 2

Setting Up Your Accounts

We used to have just one email SETTING UP ON THE

account and one computer. MAC
Now we’ve got multiple email
On your Mac, you set up new
accounts, multiple computers,
mail accounts in the Mail
and multiple other iThingies
application or through
that go in our pockets and
Internet Accounts in System
bags. Setting up your email
Preferences.
account—if you’re not used to
these things—can seem After launching System
daunting but it’s not. Anyone Preferences and clicking
can do it in Apple Mail. Internet Accounts (under
Internet & Wireless), you’ll
see the left pane displays
existing accounts while the

100
right pane displays services to set up new
Gallery 4.1 Apple Mail Setup Screens on the Mac
accounts. These preconfigured services
include iCloud, Microsoft Exchange, Gmail,
Yahoo, and even AOL. (There are other
services listed in this menu unrelated to
email including Twitter, Facebook, Vimeo,
and Flickr.) If, for instance, you want to set
up an iCloud account, click on the iCloud
icon in the right pane and then System
Preferences will walk you through the
setup. You can forget all about ports, IMAP
server addresses, and all the other details I
explained in the previous chapter. When
using these most common services, all you
need is your email address and password.
Here is the Internet Accounts System
Apple Mail does the rest and your account
Preferences on the Mac in 10.9
is set up. Mavericks.
However, Apple’s list of preconfigured email
services is not exhaustive. There are a lot of
email providers that didn’t get one of

101
Apple’s magic buttons. For those, you’ll Screencast 4.1 Setting Up Your Email Accounts on the Mac
need to enter your email credentials
manually. Do that by clicking the Add
Other Account... button. The application
walks you through a series of dialog boxes,
shown in gallery 4.1, which prompts you for
the details of your email account. I explain
those details in chapter 3. If you don’t have
all the details, a quick Internet search or
phone call to your service provider should
get you set up. I keep notes on all my email
accounts in 1Password (iOS App Store) email accounts on the Mac from inside
(Mac App Store) (website) so when setting Apple Mail by clicking Mail on the Mail
up a machine, I’ve got everything I need. menu bar and clicking Add Account… or
Once you get to the end of the dialog boxes, Preferences.... Click on the Accounts tab
Apple Mail will see your and then the plus sign (+) at the bottom-left
new email account, and portion of the dialog box. This opens a
you can get back to series of dialog questions very similar to
work. those found from the System Preferences
screen explained earlier. In fact, once you’re
You can also set up new done setting up the email account, that

102
account will show up in System Preferences SETTING UP ON THE IPAD AND
under Internet Accounts. Screencast 4.1 IPHONE
demonstrates setting up an email account on
Managing email accounts on the iPad or
the Mac.
iPhone does not take place in the Mail app.
Instead, you’ll find the account tools in the
Settings app in the Mail, Contacts,
Calendars screen. This screen includes
several settings and preferences for your
mail accounts. For now, just look at the top,
which includes a list of accounts. (See
gallery 4.2.) Tapping on an existing account
slides in a screen with additional options
and settings for that account. The iCloud
account settings are, not surprisingly, the
most extensive since iCloud is an Apple
product, and its services reach deep into the
Mac and iOS operating systems.
Particularly relevant to this book is the Mail
switch. If you turn it off, your iCloud mail
disappears from Apple Mail. Switching it

103
back on returns it. This on/off function with iCloud, you’ll be prompted for your
works for all of your installed mail accounts. Apple ID and password. That’s it. Tap in
This can come in handy. For example, when those two items and you’re set. Often these
truly on vacation or even just spending an third-party services will also provide you
afternoon with my family, I’m not above calendars, contacts, notes, and other
simply turning some email accounts off. services as part of your account. If they do,
you’ll be prompted with the account setup to
To add a new email account, tap
choose which services to turn on. Only turn
Settings→Mail, Contacts, Calendars→ Add
on those services you plan on using. If, for
Account.... This opens the Add Account... instance, you love your Gmail account but
screen shown in gallery 4.2. For setting don’t plan on using
up accounts with the most common Google’s calendar
email providers (including service, turn it off. If
iCloud, Microsoft you have three
Exchange, and calendar services
AOL), you simply turned on but only
need to pick the use one, you are
provider and enter inevitably going to put
your account details. an event in one of the
For example, when dormant calendars, miss your
setting up an email account nephew’s Eagle Scout ceremony,
104
have your sister Gallery 4.2 “Other”. Tap
angry at you for six Other and then tap
months, and then the Add Mail
not get a very good Account button.
birthday present Apple then
from her. So as you presents you a
can see, turning off series of entry
redundant, unused boxes with
services always descending levels
leads to better of nerdiness. The
presents. first is the easiest,
asking for your
If you’ve got an
name, then email
email account with
This is the first email setup screen, letting you address, password,
a provider not
choose between available services. and an account
included on Apple’s
description. iOS
list, all is not lost.
will then try and
Similar to the Mac,
hook up the
there is a mechanism for manual setup.
account on that information alone. If it fails
Under the list of built-in accounts in the
(and it often does), it will take you to
Add Account... screen is a button labelled
another screen asking for more details. This
105
is where all of those account details I
covered in chapter 3 come in handy. If you
master those, you shouldn’t have any
trouble setting up an email account on your
iPad or iPhone.
Screencast 4.2 Setting Up Email Accounts on the iPad

When you are done, enable your new

account and get back to the Mail application
to make sure everything is working. Gallery
4.2 shows several screenshots on how to set
up new mail accounts on iOS. Screencast
4.2 includes a demonstration of setting up a
new mail account on the iPad.

As you can see, setting up new email

accounts on the Mac and iOS for use in
Apple Mail is not difficult. At this point you
should be able to set up all the accounts for
yourself, your family, and coworkers. That
always leads to better presents.

106
 SECTION 3

Checking Mail

CHECKING MAIL ON THE MAC sticking it to the

man, digitally.
Apple Mail checks email automatically when
They won’t see
you load the application and is set, by
any incoming
default, to accept push notifications. That
email while
means if an email service includes the ability
working. A less
1
to push an email (and notification) to your
extreme solution
devices immediately upon delivery, Apple
is to let email push to your devices so the
Mail will do so. Alternatively, you can set
messages are there when you go looking for
Apple Mail to check for new mail after a
them, but turn off all notifications so you
certain time interval or not at all. Telling
don’t hear the ding every time someone (or
your email client not to check automatically
some robot) sends you an email.
can make sense. I know some people who
turn off all email delivery when they are On the Mac, you can adjust how often
focused on a project. It’s their own way of Apple Mail checks for new email. Click

107
Mail→Preferences...→General→Check for Apple Mail on the Mac includes a unified
new messages: and choose how frequently inbox. That’s the primary inbox in Mail that
you’d like to check for new mail. You can combines inboxes from all of your active
set this for each individual email account. email accounts. You can also check for
specific accounts if that makes more sense
for your workflow. On the Mac, if you find
yourself frequently accessing a particular
Setting the Email Frequency in Apple Mail
inbox—or any email folder for that matter—
drag it up to the toolbar. This is a more
recent feature in Apple Mail for Mac that
allows you to quickly access your most
frequently accessed folders. They’re always
up in the toolbar, and you can click on them
at any time. Even better, you can access
each toolbar mail folder with a key
combination. To do so, hold down the
Command key and press the number key
corresponding to the folder on the toolbar.
The first folder will be Command+1, the
second folder will be Command+2, and so
on. For instance, in the screenshot below,
108
 The Command Plus Number Trick

Screencast 4.3 Checking Email in Apple Mail and Navigating

Command+3 will jump to the Action folder. Mailboxes with Keyboard Shortcuts

I use this feature all the time to move

between my mail folders.

Screencast 4.3 demonstrates how to check

your mail on the Mac and move between
email folders.

109
CHECKING MAIL ON IOS
The Apple Mail app on your iPhone and iPad checks for new Gallery 4.3 Setting Email Frequency on
messages automatically by default. It also has the option to Apple Mail for the iPhone and iPad

change this setting to time intervals or not at all. On the iPhone

and iPad, tap Fetch New Data in the Mail, Contacts, Calendars
screen, shown in gallery 4.3. On this screen, you can set new
data preferences for each mail account. For instance, you could
set your Microsoft Exchange account to push mail at you
whenever it is received and set your personal email account to
only fetch new mail when you specifically request it. Or better
yet, the exact opposite of that. It is worth noting that these push
settings are done not just by account but also by mailbox. You
could, for instance, push your inbox and Action mailbox but
leave your Archive mailbox alone.

Apple Mail on the iPad and iPhone also has a unified inbox.
This wasn’t true with the original release of iOS, and its
addition was welcomed by those of us with multiple email
addresses. One nice addition with iOS 7 is customization of the
mailbox view in iOS Apple Mail. By default, this screen
displays the unified inbox along with specific inboxes for each

110
of your email accounts, the VIP mailbox, the Mac (explained later), these
and flagged messages. However, tapping the preformatted folders are useful.
Edit button in the top-right corner lets you
Another nice addition in iOS 7 is the ability
turn off any mailbox you don’t use. For
to place some of your favorite email
instance, if flagged messages aren’t your
mailboxes on this screen. For example, that
thing, you can turn off the flagged message
Action mailbox that I keep yakking about is
mailbox. (I so rarely flag messages that I’m
tempted to turn it off.)
Screencast 4.4 Checking Email and Setting Up Custom Folders
You can also turn on additional email boxes on the iPhone and iPad

that provide different windows into your

email. There is an Unread box that displays
all unread email from your inboxes. There is
another view, labelled “To or CC”, that only
shows messages addressed or copied to you
directly. There are also options to display all
messages with attachments, all draft
messages, all sent mail, and all trash. While
iOS Apple Mail doesn’t have the Smart
Folders you can create with Apple Mail on

111
on this screen on my iPhone. To add a
mailbox, tap the Add Mailbox… button in
the Edit screen, navigate to the mailbox you
want to add, and tap on it. I’ve added
several of my most used mailboxes to this
list and it makes iOS mail management
much easier.

Screencast 4.4 demonstrates how to check

your mail on the iPhone and iPad, move
between email folders, and set up and use
custom folders on iOS Apple Mail.

112
DATA DETECTORS Apple Mail Data Detectors in Action

Data detectors are one of the most useful

features of Apple Mail. The application is
always studying your incoming email for
phone numbers, addresses, or calendar
items. On the Mac, hover your mouse on
the information, or on iOS, tap on it, and
Apple Mail presents you options. Phone
numbers can get added to existing or new
contacts. Apple Mail will also display the
phone number in large type across the
screen. An address may get added to a
contact or displayed in the Maps application
(new in OS X Mavericks). Calendar events
get added to your calendar. Data detectors
contacts and calendar events. Screencast 4.5
also work with shipment tracking numbers
shows how to work with data detectors.
such as FedEx and the U.S. Postal Service;
clicking on it gives you the option of
tracking your package. I use data detectors
nearly every day for updating and adding

113
SETTING APPLE MAIL iPhone give you plenty of control over
NOTIFICATIONS notifications.
Notifications are a big deal. I talked about
this in the Chapter 2 discussion of tactical NOTIFICATIONS ON THE MAC
email. There must be someone at Apple who In Apple Mail on the Mac, click
agrees with me because the most recent Mail→Preferences...→General→New
versions of Mail on the Mac, iPad, and
messages sound:. Set to None and banish
the ding from your life. I leave the Play
Screencast 4.5 Using Apple Mail Data Detectors sounds for other mail actions option
checked because the whooshing sound of
sent mail satisfies something deep within my
soul. Turn off Dock unread count: if you’d
like, or point it at different Smart Folders.
I’m going to explain Smart Folders in detail
later in this chapter.

114
 Gallery 4.4 notification pop on your Mac’s screen every
time you start getting some work done? I
have the attention span of a puppy and
those notifications cause me nothing but
trouble. I can be sitting there, working hard
on the final equation for a drug to prevent
people from using the word literally in every
sentence. Then, suddenly, my Mac gives me
a notification that I’ve received an email for
30% off yack-herder shoes and I’ve lost it.
My miracle cure has literally left my head,
and I’m back to the drawing board. I’m sure
You can turn the message sound off in the there are studies, but I don’t need to link
General tab of Apple Mail’s preferences. them. Everyone reading these words has
experienced the loss of concentration that
comes with little interruptions. I recommend
turning the notifications off entirely.

OS X for Mac now gives users pop-up Unfortunately, turning off notifications isn’t
notifications just like iOS does. It’s a terrible possible for everyone. Maybe you’ve got a
idea. Can you imagine getting an email crazy boss that expects you to reply to

115
emails within minutes or a sick relative. In
that case, set those people who are
important enough to merit your immediate
attention as VIPs (covered later in this
chapter) or use a service such as AwayFind
(covered in chapter 3) and limit Screencast 4.6 Setting Email Notifications on the Mac

notifications to just those people. Respect

yourself. Protect your focus and attention.

Gallery 4.4 shows notification screenshots

on the Mac and screencast 4.6 walks you
through notification setup on the Mac.

116
NOTIFICATIONS ON IOS Email Notification Settings on the iPhone

On your iPad or iPhone, go to the Settings app, tap the

Notifications button, and then tap the Mail button to see
the Mail notifications. The first setting lets you adjust the
number of unread messages to display in the notification
screen that appears when you drag down from the top of
the screen.

You can then set specific notifications in relation to each of

your email accounts. Do you want to get badges and
notifications from your work account but not your
personal account (or the opposite)? Adjust your accounts
accordingly. I turn off nearly all of my notifications.

There are three types of alerts: (1) Banners, which show

up at the top of the screen and fade out after a few
seconds; (2) Alerts, which appear in the center of the
screen and don’t go away until you tap the screen to
dismiss them; and (3) None (my beloved), which gives
you no notifications. In this screen, you can also turn off
new mail notification sounds and the badge that appears

117
on the mail icon. I really dislike both of
these distractions and did my own private
happy dance when Apple gave us the option
to turn them off. The new email badge on
my iPhone is one of those things I am Screencast 4.7 Setting Email Notifications on the iPad
absolutely powerless to resist. Turning it off
removes the temptation.

The final two iOS notification-related mail

settings let you choose to show a preview of
the message in notifications and whether or
not notifications show when your iPhone
and iPad are locked. I’ll leave these up to
you, but be warned: if you have any concern
for your email security, letting your device
display messages when they are locked
probably isn’t a good idea. Screencast 4.7
demonstrates email notification settings on
the iPad.

118
 SECTION 4

Filing Email in Apple Mail

So let’s say an email lands in your inbox and time. It also requires you to lift your hands
you deal with it. You and that email are at from the keyboard, which slows you down.
peace with one another. How are you going Not only that, it entails a very fine mouse
to file the email away? There are several gesture. Those folders in
ways to do that on the Mac, iPad, and your sidebar are
iPhone. not very
large, and if
FILING EMAIL ON THE MAC you’re not
careful, you
The most common method for filing email
will drop
on the Mac is clicking it with the mouse and
dragging it to a destination folder in your
sidebar. That is, however, the worst way to
file your email. Using the mouse to click and
carefully drag to a folder requires extra

119
emails into the wrong folder. In fact, even if
you are careful, you will occasionally drop The Control + Command + Number Trick

emails into the wrong folders. Even worse,

you won’t always notice when you make
that mistake. Then later, when you go
looking for the email, it will be missing and,
at best, you’ll spend even more time hunting system, Apple has added its own keyboard
for it. If you take an email that you meant to shortcuts to Apple Mail. Remember those
place in your Action folder but accidentally keyboard shortcuts I explained above
place it in your trash instead, you’ll never concerning accessing email folders? They
respond and look like a flake to somebody. also work to move email messages to those
There are better ways to file email on your folders. Where the Command key and a
Mac that are faster and more reliable. Part corresponding number will jump to a folder,
of becoming an email pro involves mastering Control, Command, and a corresponding
these. Until recently, the only way to number will move the current email to the
automate filing email with keyboard folder. This makes filing email easy with the
shortcuts in Apple Mail required a third- keyboard. For instance, you could be in
party application, such as Mail Act-On your inbox and see an email from a friend
(explained later in this chapter). However, thanking you for buying her a fancy new
with recent versions of the Mac operating chainsaw, and you can send it to the Archive

120
by holding down the key combination archive a message and saves you extra room
Control+Command+4 (assuming your in your menu bar.
Archive is the fourth folder in your toolbar).
Screencast 4.8 demonstrates how to move
There will be no messy mouse clicking and
email messages on the Mac.
dragging and no potential for putting it in
the wrong folder. Best of all, once you
master this keyboard shortcut, you will do it
automatically. This is how I
file email in Apple Mail on Screencast 4.8 Filing Email on the Mac

my Mac, and it is really fast.

It becomes muscle memory
and you can zip through
your email quickly. Some
users even give the
mailboxes names mathching
their position. (e.g., “1-
Action”)

Another great keyboard

shortcut is Control
+Command+A, which will

121
FILING EMAIL ON IOS
Filing an Email on the iPhone
Filing email on your iPhone or iPad requires
manipulation of the touch screen. This is different from
keyboard shortcuts and probably a bit slower but also
more reliable than using the mouse on the Mac. Simply,
there are trade-offs.

Viewing an email you’d like to file on your iPhone or

iPad, tap the Folder icon in the toolbar at the bottom.
This will bring up the menu showing a list of all the
folders on that particular account. Tapping any one of
those folders will move your message to the destination
folder. If you would like to move the email to a different
account, tap Accounts in the top-left corner of the screen
(or swipe from the left side of the screen), and that will
bring you to a list of all of your email accounts. From
there you can select a different email account and get
that email account’s list of folders. Tap the appropriate
folder in the other email account, and iOS Mail will send
your email there. If at any point you decide you don’t
want to file that email after all, tap the Cancel button,

122
and you’ll go select a few (or
Screencast 4.9 Moving Email Messages in Apple Mail on the iPad and iPhone

back to your all) of your

email. emails. As you
tap each circle,
If you’re
it fills in blue
already a
with a white
keyboard junkie
check mark.
on the Mac,
You can also
tapping and
select all
filing each
messages with
individual email
the Mark All
will start to
button. Tapping
make you crazy.
the Mark All
Fortunately,
button also gives you options to flag or mark
iOS Mail has a solution for processing
messages as unread. Once you’re done
multiple emails at the same time. To do so,
selecting messages, iOS Mail gives you
while viewing your email list, press the Edit
options to trash the selected emails or move
button on the top-right corner. iOS Mail
them to a different folder using the same
then moves all of your emails slightly to the
mechanism for moving a single message.
right on the screen and inserts empty circles
next to each message. Tap on the circles to

123
Another recent improvement in Apple Mail
is the ability to process email without
opening it. If you swipe slowly from right to
left across an email in your message list, iOS
presents Delete and Flag buttons. There is
also a More button. Tapping that opens
additional options for processing email such
as Reply to All, Forward, Flag, Mark as
Read, Move to Junk, and Move Message...
buttons. This gesture has become second
nature for me and I use it to blast through
my inbox on my iPhone daily. In iOS 8,
Apple added an additional gesture for left to
right where you can mark a message as read
or send it to the archive. This preference is
set in the Mail Preferences screen in
Mail→Swipe Options.

124
Another common problem with Apple Mail
on the iPad and iPhone before iOS 7 was
accidentally filing emails in the trash or
wrong folder. When that happened, you had
to navigate to the misfiled folder (or trash),
find the lost email, and then manually move
it to its proper location. That was really time
consuming. Now if you misfile a message,
shake your iPhone or iPad like you are
auditioning for a salsa band. The iPhone or
iPad will then prompt you to undo your last
move. (In case you didn’t know it, shake to
undo is a common but little known gesture
in many iOS applications.)

125
 SECTION 5

Searching Apple Mail

So you’ve mastered reading and filing email the screen (or press Option+Command+F)
messages. How about finding them? Apple and start typing your search. For me, this
Mail also has some great tools for this usually starts with typing a person’s name.
purpose. As you start typing a name, Apple Mail will
compare it with with its
SEARCHING EMAIL own knowledge of your
ON THE MAC email database. As you
continue typing, it will
Search in Apple Mail suggest names from
has come a long way in your known contacts
the past few years. In and email
order to search your correspondents. If you
email database, click in move the mouse point
the Search bar in the over that name or press
upper-right corner of
126
the Arrow Down key to select that name emails to that person in February 2013. You
and press Enter, Apple Mail then focuses its don’t have to stop there. Maybe you want to
search on that person. You can then click on look for emails to that certain person during
the front of that person’s name and select February 2013 containing the word ornery.
To, From, or Entire Message. If you select To the right of your date token, type
“To”, you’ll only see emails you sent to that ornery and select Any. You can also
person. “From” displays emails from that narrow a search to a specific mailbox by
person. “Entire Message” displays any clicking on it in the sidebar or the toolbar,
emails that have that person’s name (even if assuming you’ve put some of your mailboxes
they weren’t written by or to that person). in the toolbar. There are more search tokens
That search is contained in a small rounded than name and date.
rectangle in the Search bar. That is called a
search token.

The great thing about email search tokens is

you can use more than one of them. Say, for
instance, you wanted to look for emails to a
certain person but just emails for the month
of February 2013. Type in February
2013 to the right of the existing name
token, and then Apple Mail will look for

127
Here’s a rundown of search tokens: list of emails with those types of
attachments.
Name
All Text
Search for a name including messages sent
to or from that person, or in the entire If you don’t select a specific token, Apple
message. Mail will search the entire message.

Date Using the above criteria, I’m usually able to

find anything I’m looking for. There is more
Search for a specific month (February
you can do, though. The Search bar follows
2013), year (2013), and even date range
Boolean logic (AND, OR, NOT). Boolean
(2/1/13-3/15/13).
terms must be in all caps to work. You
Subject could, for instance, search for an email
message that contains pork chops AND
Look for particular words in the email’s applesauce. The Boolean term NOT will
subject line. exclude any email with that term in it. The
Attachments minus sign (-) in front of a word works the
same as NOT. For example, pork chops
Type PDF, Keynote, iWork, Doc, Excel, AND applesauce -peter looks for an
or any other file format you like in the email containing the words pork chops and
Search bar and Apple Mail will give you a applesauce but not the word peter.

128
Remember these email searching tricks you see now why I’m against making big
because they are going to help you make heaping piles of email folders? It isn’t that
some great Smart Mailboxes, covered later hard to search out email anymore.
in this chapter. Screencast 4.10 demonstrates using search
tools in Apple Mail.
As you can see, with a little effort you can
drill down pretty deep, pretty quickly. Can

Screencast 4.10 Using Search Tools in Apple Mail on the Mac

129
SEARCH EMAIL ON THE IPAD AND IPHONE
Searching Apple Mail on the iPhone
Searching email on the iPhone and iPad is done through
the Mail Search bar. To get there, go inside any mailbox
on your iPad or iPhone and pull it down. This exposes
the Search bar. Type in your search term, and your
iPhone or iPad will search for you. There are buttons to
conduct the search in the current mailbox or in all of
your mailboxes. There are no search tokens on iOS
devices like those found in Apple Mail on the Mac.

The iPhone or iPad will report back immediately with

any matching emails currently downloaded and then
start searching your email server for any additional
email messages. This illustrates one of the issues with
email on the iPad and iPhone. On your Mac, all of your
emails exist on your hard drive; that isn’t the case on the
iPhone and iPad. These portable devices have limited
storage capacity, and some people (like me) have a lot of
email. Apple, wisely, doesn’t want someone with a 12GB
email database to be left with only 4GB on a 16GB
iPhone, so the iPhone and iPad don’t download all of

130
your email. Instead they download only the the Mac version without those great search
most recent emails and access the rest tokens. On the brighter side, with iOS 7,
through the email database. That involves searching mail on iOS devices got a lot
going to the Internet and slows you down a faster. Screencast 4.11 demonstrates using
bit. iOS Apple Mail also isn’t as powerful as search tools in Apple Mail on the iPad.

Screencast 4.11 Using Search Tools in Apple Mail on the iPad

131
EMAIL FLAGS with an alarm klaxon going off. Fortunately,
that is pretty rare, but it is nice having that
Flagging an email now may help you find
tool available when necessary.
that email later in Apple Mail. A flag is
simply a marker that tells Apple Mail “I am Screencast 4.12 demonstrates setting and
special”. Apple Mail has built-in filters that using flags in Apple Mail.
will display only flagged messages. In Apple
Mail on the Mac, there are several different
colored flags to choose from. Unfortunately,
the colored flags all show up in iOS Apple Screencast 4.12 Setting and Using Flags in Apple Mail
Mail as orange.

I rarely use flags. Because I’m pretty

regimented in the way I handle email, I find
I simply don’t need flags that often.
Occasionally, however, I will get swamped.
My email will start to accumulate, and I
simply won’t have time to process it
properly. If I’m buried like that and see an
email that is very important but something I
can’t deal with immediately, I will flag it for
later. To me, a flagged email truly is an email

132
 SECTION 6

Writing Email with Apple Mail

You wouldn’t think there is any reason to http://www.google.com/url?sa=t&rct=j&q=

%20paperless&source=web&cd=2&cad=rja&ved=
include a section on how to write an email.
0CEcQFjAB&url=https%3A%2F
We’ve all been writing email for years. In %2Fitunes.apple.com%2Fus%2Fbook
chapter 2, I explained a better order for %2Fpaperless%2Fid520393162%3Fmt
writing email messages. There are, however, %3D11&ei=7YT6UayMLKWEiwKfuYGACw&usg=AFQjC
NEhQPcZNamr58mqY4hlDQELR_2NDw&sig2=sigjrn
a few tricks you should be aware of when rpdHiPa3J2uCkrzA&bvm=bv.50165853,d.cGE
writing email in Apple Mail.
Not only is it inscrutable, it also takes a lot
THE EMBEDDED HYPERLINK of characters so it may end up on more than
one line in your email client. Sometimes
Quite often you’re going to want to link email clients on the other end will look at
something in an email. The trouble is a lot of that line break and not realize it is a
links on the Internet are pretty ugly. Here’s hyperlink, so the recipient not only gets an
an example of a link for my Paperless book in ugly link in the email, they also get a broken
the iBooks Store:

133
 Screencast 4.13 Creating Embedded Hyperlinks in Apple Mail on the Mac

one. In Apple Mail, you can fix this with down the Command+K keys
embedded hyperlinks. With an embedded simultaneously, and Apple Mail opens a
hyperlink, you can type a small bit of text window for you to paste in your link. When
and then bury in that text a hyperlink to you’re done, the text will display with a
somewhere else. The magic key combination different color and your recipient will know
for doing this on the Mac is Command+K. to click on the link to go off into the
Highlight the text you want to link, hold Internet. You can also create an embedded

134
link through the Apple Mail menu at QUOTING LIMITED TEXT IN A REPLY
Edit→Add Link... path. There is one
Another nice touch in Apple Mail is the
downside to embedded links. If your ability to quote a limited portion of an email
recipient forwards the message, the next in your reply. Let’s say you receive a 2,000-
recipient can’t use it. They don’t work in word email, in the middle of which is buried
forwarded messages. a single question. If you highlight the
Embedded hyperlinks on iOS aren’t as easy. question and press Reply, the draft reply
There is no current mechanism in iOS will only include the selected question as
Apple Mail to embed a hyperlink. There is, quoted text. This makes for a much cleaner
however, a way around this. There are response. This trick works on the Mac,
several third-party text editors that support iPad, and iPhone versions of Apple Mail,
creating hyperlinks, and some of those will and I use it every day.
export directly to a new mail message. I
demonstrate this using Drafts in chapter 6,
where I include screenshots showing how to
create an embedded hypertext link.

135
Moreover, using selected text for a reply is a
great way to kick off an inline reply,
explained in chapter 2.

SETTING AN EMAIL’S SEND-FROM

ADDRESS
on the one you want to use and continue
Because most of us have multiple email composing your message.
accounts, we are going to occasionally need
to set the account we want the email to be This works fine for most people but for
sent from. It doesn’t make sense to send an those of us who are impatient and don’t
email to a client from your personal address, want to lift our hands off the keyboard to
and it doesn’t make sense to send an email to change the email send-from account every
your friend from your work address. time we want to send a message, you can
create a keyboard shortcut on the Mac. In
On the Mac, in the compose email dialog order to do this, go into the System
box, there is a selection box above the Preferences pane on the Mac and create a
message body window where, with your keyboard shortcut. You can create one for
mouse, you can click on the email address each of your email accounts and then tie
you want the message to be sent from. Click them to a keyboard combination. I do this
for all of my email accounts and find it much

136
quicker for changing the send-from address
before firing off my emails. Screencast 4.14
demonstrates how to do this.

Changing the send-from account on an

iPhone or iPad requires tapping the Cc/Bcc,
Screencast 4.14 Setting Keyboard Shortcuts for the Email
From: field at the top of the message. This Send-From Accounts in Apple Mail
unfolds to show each of those fields. You
can then tap the From: field and select the
email address from which you want to send
the message. This is also how you add
carbon copy (Cc) and blind carbon copy
(Bcc) recipients. One of the improvements
to iOS Apple Mail with iOS 7 is a sort of
logic where Apple Mail predicts which email
account you want to send from. If you are
sending an email to a coworker, for instance,
the app is likely to set your work account as
the send-from account. It is right more often
then not, but you still should keep an eye on
what account you are sending from.

137
ADDING ATTACHMENTS screen with your mouse until Spaces moves
over to the Mail screen. If you find this as
You can add an attachment to an email
vexing as I do, get a copy of Unclutter (Mac
message on your Mac by clicking the Paper
App Store) (website), Yoink (Mac App
Clip icon button and selecting the
Store) (website), or one of the myriad other
attachment from your Mac. You can also
apps available in the Mac App store
drag a file into the body of your message,
designed to solve this very problem.
and Apple Mail will add it as an attachment.
I’ve become so reliant on dragging Another nice touch in Apple Mail is the
attachments into messages that when I use ability to set the size of a photo attachment
an email client that doesn’t support this, I for your email. With rapidly-increasing files
find it jarring. When working with Apple size of photos taken by modern digital
Mail in full screen mode, dragging cameras, it can make a lot of sense to reduce
attachments into messages gets trickier. You the file size of photo attachments.
need to pull the file to the edge of your

138
On iOS, adding attachments is not as application. From there, tap the Sharing
intuitive. Tap and hold inside an email button to share the subject PDF file via
message, and Apple Mail provides a pop-up email. That creates a new email message and
with the option to insert a photo or video attaches the file. This isn’t particularly
file. It does not, however, give you the intuitive but it works. This is one thing I'd
ability to insert a PDF or other type of file. like to see get easier with future versions of
In order to do that, you need to open an iOS Apple Mail. Screencast 4.15
application on your iPhone or iPad that demonstrates how to use email attachments
manages the source file. For instance, for a in iOS.
PDF file, open your favorite PDF

Screencast 4.15 Making Email Attachments in iOS

139
With OS X Yosemite, Apple added the
ability to send large attachments from
iCloud accounts using Mail Drop.
Normally you cannot attach large files
to emails. Most email servers choke on
anything larger than 10MB which, in
this day and age, isn’t very large.

With the addition of iCloud Drive,

Apple Mail now has the ability to
automatically upload oversized
attachments to iCloud Drive and serve
that to a recipient via a link. This is an
improvement over existing solutions
that require you to separately upload
and create a link for embed. If your
recipient is also an iCloud subscriber,
their Apple Mail will automatically
download the attachment making the
process even easier for users.

140
MINIMIZING EMAIL DRAFTS ON
IPHONE AND IPAD
One problem that always drove me nuts on
iOS is the way I'm locked down as soon as I
start composing an email. Traditionally, you Screencast 4.16 Minimizing Message Drafts in iOS
couldn’t, for instance, go refer to a different
email message while composing a new one
short of saving the message as a draft and
completely backing out of the composition
screen.

With iOS 8, you can now swipe a draft

message’s title bar down and it will park
itself at the bottom of the screen. You can
then look through other messages and then
go back to your compose window by
tapping in the title bar at the bottom of the
screen This even works for multiple
messages.

141
USEFUL MAC KEYBOARD Shift+Option+Command+V
SHORTCUTS pastes text and matches the current style.
This is useful when pasting text copied from
There are several more useful keyboard
your browser.
shortcuts when
writing a message in Shift+Command+T
Apple Mail on the sets the current
Mac: message to plain text
mode and removes
Command+S
all formatting.
saves the current
message. Command+K
inserts a hyperlink
Shift+Command+D
for the selected text
sends the current
to a website or
message.
download link.
Shift+Command+: Screencast 4.13
(Colon) demonstrates this.
toggles spelling and grammar.
Control+Option+Command+P
Shift+Command+V saves the currently selected email to PDF.
pastes text as a quotation.

142
In addition to these, you can also create a
keyboard command for any menu item in
Apple Mail using your Mac’s keyboard
shortcut feature, as demonstrated in
screencast 4.14.

As a bit of advice about keyboard shortcuts,

don’t try and learn all of these shortcuts in
one go. Pick a few that you can use often
and get comfortable with those. Once they
are second nature, pick a few more. Before
long, you’ll be flying through Apple Mail
without lifting your hands from the
keyboard.

143
EMAIL SIGNATURES
Automating signatures in your email is one
of the easiest ways to save yourself a lot of
time. Every email you send is going to
include a signature. Why not have the
computers do this for you? I explained at
length the good, the bad, and the ugly of
email signatures in chapter 2. So how do
you go about setting up an email signature
in Apple’s Mail app?

accounts and even have multiple signatures

EMAIL SIGNATURES ON THE MAC per account. If you do that, when writing an
Go to Mail→Preferences... (or press email message, Mail will give you the option
Command+, [Comma], which opens to select which signature to use with your
Preferences in most Mac applications). outgoing mail. You can also check the box to
Then select the Signatures tab. From here have Apple Mail match the typography of
you can start adding stock email signatures. the mail message with the inserted
Tap the Plus (+) icon button and go to town. signature.
You can attach signatures to specific email

144
Using Apple Mail’s built-in signatures hands are already on the keyboard, they are
makes a lot of sense if you have just one much faster. Screencast 4.17 demonstrates
signature you always use. I have several how to set up email signatures and use
different stock email signatures: TextExpander on the Mac.

XOXO, David

Your pal, David
Screencast 4.17 Setting Email Signatures on the Mac

With kind regards, David

Cordially, David
I don’t particularly like you, but I’m sending
this anyway, David

Rather than setting these up in Apple Mail,

which requires a lot of keystrokes and
mouse movements with each message, I use
TextExpander (website) snippets. For
instance, typing yp, triggers Your pal, David.
Because the TextExpander signatures are
triggered by key combinations and my

145
EMAIL SIGNATURES ON IOS

Mail signatures are managed on iOS in the

Mail, Contacts, Calendars tab of the
Settings application. In this window, you
can set a single signature for all accounts or Screencast 4.18 Setting Email Signatures on the iPad

specify a separate signature for each mail

account. Since Apple doesn’t support
TextExpander touch (iOS App Store)
(website) in Apple Mail for iOS, I use this
feature on my iOS devices for all of my
email accounts. For my day job, I have a
signature that includes my name, my
company name, and my phone number. For
my personal and MacSparky accounts, the
autosignature just signs David. I can then
dictate in the closing or use iOS’s keyboard
shortcut feature. Screencast 4.18
demonstrates email signatures in Apple Mail
on the iPad.

146
APPLE MAIL STATIONERY
Apple Mail Stationery on the Mac

Several years ago, Apple added stationery to

Apple Mail. When composing a new
message in Apple Mail on the Mac, you’ll
see a Stationery icon button on the far right
in the toolbar. (It looks, not surprisingly,
like a very small piece stationery.) Clicking
on that opens up a series of formatted
stationery forms to choose from. They have
multiple themes including birthdays,
announcements, photos, sentiments, and
plain old stationery.

You can select any of the professionally

designed stationery, replace the stock text
and images with your own, and then send it
off. It makes for a very attractive email. It Apple Mail. There are some third parties
works pretty well, and it even displays that sell additional stationery forms for
properly in webmail clients. I often use it to Apple Mail. Equinux (website) has one of
send birthday greetings to friends. This is the biggest selections of additional
another feature that’s only available in stationery.
147
USING HANDOFF
With iOS 8 and Yosemite, Apple added a
new feature called “Handoff” that let’s you
start work on one device and continue it on
another. Let’s say, for instance, you are
working on a long email response when you
suddenly get called away from your Mac.
Using Handoff, you could open your iPhone
or iPad and a Mail icon shows up in the
lower-right portion of the lock screen.
Swipe that up and your Mac hands off the
draft email to your iOS device and you can
pick up where you left off. I originally
thought this was a gimmick but now I find
myself using it all the time with Apple Mail.

148
 SECTION 7

Apple Mail VIPs

One of the challenges of email— applications will treat them with

perhaps the challenge—is
separating the wheat from the
chaff. We have these email
addresses, which are often public,
VIP special love and care. There is a
separate email folder that holds VIP
email. This way, if you only have a
few minutes, you can check just the
and anyone (or any robot) in the world can VIP box and make sure there is nothing
send something to us asking for our important from people you consider
attention. Some of those messages are from important.
kind, emotionally mature humans. Many are
You can also customize notifications settings
not.
on the Mac and iOS so that you only get
To help solve this problem, Apple added notifications from VIPs. This is an excellent
VIPs to Apple Mail. You can mark someone way to minimize distractions and still get the
such as your spouse or crazy boss as a VIP, notifications you need. If you turn off all
and the Apple Mail Mac and iOS notifications except for your spouse, your

149
crazy boss, and your favorite clients, then an Intelligently using VIPs, you can go back
email notification means something to you. and turn on those notifications I kept telling
It is more than an unwanted distraction. you turn off earlier. Just make sure the
notifications are for VIPs only.
I think VIPs were a great addition to Apple
Mail and use them often. It is one of those
features that make it hard for me to consider
leaving Apple Mail as my primary email
client. In addition to having my family and
coworkers set as VIPs, there are some
clients and friends who have made the cut. I
frequently put people on the list SETTING VIPS ON THE MAC
temporarily. If I’m in the middle of a
The easiest way to make someone a VIP in
contract negotiation, I’ll make the other
your Mac is to hover the mouse cursor to
lawyer a VIP and then remove her from the
the left of their name on your email list or in
list after we are done. If I’m about to record
an email message. The outline of a star
a Mac Power Users episode with a guest, I
appears. Click on it and the outline of the
make that guest a VIP so I’ll know
star darkens. Congratulations, you just
immediately if she emails me. If you are
made that person a VIP. You can also do
using Apple Mail, you should start using
this by tapping the Arrow to the right of
VIPs both early and often.

150
their name and selecting Add to VIPs. To Apple Mail ships with a useful VIP Smart
remove the person from your VIP list, do Mailbox that allows you to easily see all VIP
the same. It is so easy to add and remove email.
people from VIPs that there is no reason not
to use it aggressively. Don’t put yourself in a
Screencast 4.19 Using Apple Mail’s VIPs for Fun and Profit
rut of picking a few people and forgetting
about it. Instead, make your VIP list
dynamic, and look constantly at your email
recipients for potential temporary VIP
users. Once you add someone as a VIP on
your Mac, any email from that person (from
any of their accounts) will get the VIP
treatment. Because you are letting VIP
contacts through your email firewall, this
allows you to have your cake and eat it too.
Specifically, you can get rid of most email
notifications while only keeping those that
you really need.

151
SETTING VIPS ON IOS
You can set someone as a VIP on either
your Mac or iOS device and iCloud will
keep track for you. On your iPad or iPhone,
tap on the person’s name in the Address bar,
and a pop-up menu appears that includes
the option to add the person to your VIP list
by clicking Add to VIP. It works the same
for removing people from your VIP list.

Screencast 4.19 demonstrates creating VIP

users and some of the advantages of having
an active VIP list.

152
IMPORTANT MAIL THREADS
Starting with iOS 8, Apple Mail lets you
designate specific email threads as very
important in addition to emails from people
you designate as VIP.

To set a thread as important, tap the flag

button at the bottom-left of the screen while
viewing an email in the thread. Then tap
Notify Me. Apple Mail puts a little alarm
bell icon on messages in the thread and
when a new one arrives, you get notified.

If you are trying to close a deal or expecting

to meet someone, this is an excellent way to
get messages without having to make every
person in the thread a VIP.

153
 SECTION 8

Smart Mailboxes

So far, I’ve spent times? That’s

plenty of time right. I’m talking
preaching about a mailbox
against having that defies the
too many laws of mailbox
mailboxes in physics. I’m
your mail setup, talking about
but what if there was a special sort of Smart Mailboxes on the Mac version of
mailbox that didn’t require you to move Apple Mail.
messages into it but instead simply made its
Smart Mailboxes are not a destination for
own lists of messages that it thought you
mail like an Archive or Action folder would
should read? What if you could use several
be, but instead a sort of filter that scours
of these special mailboxes and even have a
your email messages collecting just those
single email show up in them multiple
that you want. Easy to use, Smart

154
 Smart Mailbox Search Criteria
Mailboxes look on your Mac. That lets you
through all of your select from creating a new
various mail files conventional mailbox (that
and displays only resides on your POP or IMAP
those emails with an server) or a Smart Mailbox.
unread status. If you are using Click Smart Mailbox.
some of the advanced Alternatively, select
techniques taught in this book, Mailbox→New Smart
you are going to have unread Mailbox... from the Mail
mail all over your system. If you Menu bar. Apple Mail creates
really want to see what’s new, a new Smart Mailbox. You can
this simple Smart Mailbox give your new Smart Mailbox
solves the problem. Gallery 4.5 a clever name and start setting
includes the setup screen for a up its filter criteria. Conditions
Smart Mailbox displaying all may include the sender,
unread messages. You can go a recipient, and other recipients.
lot deeper though. Using this, for example, you
could make a Smart Mailbox
To set up a Smart Mailbox, click
that only has messages from
the Plus icon button in the
your partner. Apple Mail will
lower-left corner of Apple Mail
also look at the date viewed,
155
last read, and what account it came in on. to, what mailbox it is in, and its
You can filter a Smart Mailbox on a attachments. Using these criteria creatively,
message’s priority and flag status (or lack you could develop some pretty useful filters.
thereof). The list goes on with filters based For instance, if you are working on a
on whether or not the message was replied project, you could create a group of the
Screencast 4.20 Creating Apple Mail Smart Mailboxes

156
 Gallery 4.5

This shows all non-junk email that is still unread.

people in your address book who are Archive folder, Action folder, or any mail
essential to that project. You could then folder you create. They will all show up in
make a Smart Mailbox that looks for all the Smart Mailbox.
emails in the last three months with just
Smart Mailboxes organize the mail for you
people from that group. It doesn’t matter
once you establish their criteria, and they
where those emails actually reside on your
are always comparing your entire email
email server. They could be in your inbox,
157
library to their rules, even the mail they’ve demonstrates how to create and use Smart
already listed. For instance, if you set up an Mailboxes and gallery 4.5 shows some of my
Unread Smart Mailbox, the act of reading a favorite Smart Mailbox recipes.
message will result in the message being
marked read, and after you are done reading
it and move on to the next unread message,
it gets booted from your Unread Smart
Mailbox. This doesn’t mean the message
moves out of your inbox, gets archived, or
anything else. The message simply
disappears from the Smart Mailbox because
it no longer qualifies for the club.

Smart Mailboxes are a great way to manage

unique or project-related mail messages.
Unfortunately, it only exists on the Mac.
Smart Mailboxes don’t appear on iOS
devices. Apple Mail for iOS does include a
predefined set of quasi-smart folders, but
these aren’t nearly as powerful as folders
you can create yourself. Screencast 4.20

158
 SECTION 9

Apple Mail Markup and Extensions

With the release of OS X 10.10 Yosemite job of figuring out what you are doing and
added a clever feature to Apple Mail that cleans it up.
lets you annotate attachments right in the
Markup is one of Apple’s first official
mail message. The feature is called Markup
implementations of OS X extensions, which
and it can make sending an image with a
arrived with Yosemite on the Mac and iOS
little doodle, or arrow, or other annotation
8. As swell as Markup is, I'm even more
loads easier.
excited about what other extension services
To kick it off, click on a file inside a mail Apple (and others) can bring to the Mac
message. An icon appears in the upper-left and iOS. Screencast 4.21 demonstrates
corner. Click it and select Markup and Apple Mail Markup.
you’re off to the races. You can draw lines,
shapes, and text. Even if you’re drawing
skills are a little rough, Markup does a good

159
Screencast 4.21 Apple Mail Markup

160
 S E C T I O N 10

Apple Mail Rules

APPLE MAIL RULES shows an inexhaustible ability to annoy

you? Rules can fix that.
I don’t know about you, but I’ve always
wished that I had my own personal robot. Rules apply a series of filters to all of your
When I was a kid, I wanted a robot to clean incoming mail. You can set very specific
my room and do my homework. These days, filters that, in turn, can apply very specific
I’m looking for a robot just to deal with the actions to emails matching your criteria.
amount of information being thrown at me Rules are the natural successor to Smart
everyday. The mail rules feature in Apple Mailboxes. Where Smart Mailboxes find
Mail is about as close as you’re going to get and display messages, mail rules find email
to having a robot to deal with email for you. messages and do things to them. For
This is perhaps the most underutilized instance, at the most basic level, you could
feature in Apple Mail. Have you received have a rule that any email coming from the
email repeatedly from someone that doesn’t domain IAmAnnoying.com gets immediately
quite qualify as spam but at the same time marked as read and sent to the trash can. I

161
Criteria for Apple Mail Rules
have a remarkable number of rules that are this simple. Every
time I get a marketing email, I create such a rule, muttering
softly under my breath, “IAmAnnoying.com, you are dead to
me.” The good news is it truly is dead to me. Anytime an
email arrives from that domain, Apple Mail marks it as read
and deletes it before I ever see it, and I never see another
email from IAmAnnoying.com.

You can also use rules to forward messages. For instance, if

you wanted to make sure a coworker gets every email from a
key client, you could set up a rule for that. It would simply
look for any email coming from a particular address.
Whenever it detects the arrival of a message from the client,
the rule springs into action. You could even color the email
red, then forward a copy to your coworker’s email address. I
demonstrate a rule similar to this in screencast 4.22.

I think a lot of people are intimidated by Mail’s rules because

most of us are not computer programmers and something this
powerful sounds like high-order wizardry. That’s not true.
Anybody reading this book can set up a very sophisticated set

162
 Apple Mail Rule Actions
of useful rules. word cockamamie, you could
apply a rule to it. There are
So how does it work? Mail’s
also filters looking for emails
rules are modular. First, pick
marked as junk, signed,
the criteria of a mail rule that
encrypted, or with high,
qualifies the message for the
normal, or low priorities.
rule. There are a lot of options
Apple Mail will even look at
including the sender, the
attachment types and names
recipient, other recipients, the
when applying rules. As you
subject line, whether or not
can see, this is a powerful set
the message is addressed to
of filters. You can combine
your full name, the date sent,
them to have filters require all
the date received, which of
or any of these criterion to be
your email accounts it was
satisfied.
sent to, whether or not the
sender is in your contacts, a Once Apple Mail finds an
previous recipient, a VIP, or a email matching your criteria,
member of a group from your there is an equally large list of
address book. That is not all. You can also things you can do with it, including copying
make a rule based on the content of the and moving the message, setting the color,
email. If, for instance, the email includes the or playing a sound. For instance, when my

163
daughter was out of town once, I had a rule new one and integrates very nicely in OS X
that would play a chime any time I received Mavericks. You can also create an
an email from her. (This was before Apple autoreply, forward, or redirect of the
added VIPs and notifications to Apple Mail message. If it is not worth your time, you
on the Mac.) You can also make the Mail can mark it as read or even delete it. If it is
icon in your dock bounce or send yourself a special, you can flag it. Finally, you can run
notification. That notification feature is a an AppleScript for when the mail arrives

Screencast 4.22 Creating and Using Apple Mail Rules

164
 My Friend-Spammer Rule
that could messages while
conceivably do still receiving the
just about important ones.
anything on your
Here is how I
Mac.
solved it with my
Let me give you spammy friends. I
another example. noticed that all of
Do you have a the spammy
friend-spammer? emails were
That is a friend that occasionally sends you copied to a whole group of people, including
an important email but much more often people I didn’t know. So I made a mail rule
spams you with snopes-worthy (website) that looked for any email from my spammy
urban myths, pictures of kittens dressed like friend that was also copied to one of these
sailors, and—of course—chain emails. other strangers. Whenever Apple Mail saw
an email matching that criteria, it marked
As a first line of defense, buy them a copy of
the email as read and trashed it. Since any
this book and tell them to stop the madness.
important emails this person sent me would
If they resist, however, you’ve still got to
not be copied to the stranger, those emails
figure out how to stop seeing their spammy
never got caught by the rule. This simple,

165
 Gallery 4.6

This rule takes those nice “someone liked you on

Vimeo” messages and marks them as read and sends
them to the archive. I like having them but don’t need
to read every one.

little rule saved me a great deal of time and and emails from your sales leads green.
aggravation. Then when you look at your email box,
you’ll be able to quickly find the emails you
Another good use of email rules is to color
need most.
your email. Make emails from your boss red

166
Setting up new rules is done in the Rules Mac trashes an incoming email from
tab of the Mail Preferences. This screen IAmAnnoying.com, that email will go to the
shows a list of existing rules but also has a trash on your iPhone at the same time.
button to create entirely new ones or even Sometimes I’ll see an email briefly appear in
duplicate an existing rule, which can be my inbox on my iPad and then suddenly
useful. This is also the window where you disappear. That always makes me smile
activate (or deactivate) existing rules with because I know my mail rules are doing
checkboxes. Screencast 4.22 shows how to their job. I know some people who keep a
set up rules of your own. Gallery 4.6 shows Mac running in their homes 24/7 partly for
the window along with some of my favorite this purpose.
rules.

Apple Mail on iOS doesn’t have rules like

the Mac does. If you’ve got a Mac at home
or in the office and use rules, leave Apple
Mail running on your Mac. Let it do the
heavy lifting for your email management.
Because you are using IMAP email accounts
(You are using IMAP, right?), the effects of
all of your rules will show up automatically
on your iOS devices. If, for instance, your

167
SERVER-SIDE MAIL RULES WITH the rule sets available in Apple Mail, users
ICLOUD could set up their rule sets in the cloud and
not have to run a separate Mac somewhere
If you are using iCloud, Apple has some
to manage email for them. As iCloud
server-side rules that operate at Apple’s
continues to grow, this is one of my biggest
servers. However, these rules aren’t nearly
feature requests: better server-side rules.
as robust as those found in Apple Mail on
Screencast 4.23 demonstrates setting up
your Mac (or Gmail’s server-side rules
iCloud Mail rules.
covered later in chapter 5). To activate
them, log into your iCloud account at
Screencast 4.23 Setting Up and Using iCloud Server Mail Rules
iCloud.com, click the Mail icon button, and
tap Rules. The cloud-based rules let you
pick just one field for the filter (you can’t
combine them like you can on the Mac).
The filter set is also more limited, dealing
with the sender, recipient, other recipients,
and the subject line. Once an email falls in
the criteria, the Apple iCloud servers will
delete, move, or forward the email. If Apple
could improve the iCloud server-side mail
rules to something like (or even closer to)

168
 S E C T I O N 11

Additional Useful Apple Mail Settings

There are some additional settings of note in Mail→Preferences.... You can also do so
both the Mac and iOS versions of Apple with a keyboard shortcut using Command+,
Mail. (Comma). The Preferences screen has a
series of tabs across the top: General,
ADDITIONAL SETTINGS ON THE Accounts, Junk Mail, Fonts & Colors,
MAC Viewing, Composing, Signatures, and
Rules. Several of these items have already
Access the Preferences panel in Apple Mail
been covered in this book, but the others are
in the Menu bar by clicking
worth a mention.

169
THE GENERAL TAB you can give Apple Mail instructions as to
whether or not it should search the trash,
In addition to setting notifications in the junk mail, and encrypted messages when
General tab, you can also change the OS X doing a search.
for Mac default mail reader. I’m going to
cover some alternative mail applications
later in this book, and if one tickles your
fancy, you set this up here in Apple Mail.
Sometimes you’ll receive calendar
invitations embedded in an email message.
There is a setting to automatically add the
events to your calendar. (I prefer to do this
manually.) OS X for Mac has a Downloads
folder in every user’s account. This is where
Apple Mail sends downloaded files by
default. If you want them to go elsewhere,
you can change it from this screen. You can
also set the behavior for what to do with
those downloads. For instance, you could
have Apple Mail automatically delete them
after you delete the related emails. Finally,

170
THE ACCOUNTS TAB

I’ve already covered setting up new email

accounts. This tab has even more settings
related to your email accounts including the
ability to turn your account on or off and
how the application manages drafts, sent
emails, junk mail, and trash. If you want to
get very specific control over your email
accounts, this is the place.

171
THE JUNK MAIL TAB

Apple Mail has its own built-in support for

detecting junk mail. I’m going to cover spam
emails in further detail later in chapter 7.
The Apple Mail junk mail filter and support
isn’t bad, but there are better options
explained later.

172
THE FONTS & COLORS TAB

If you’re not happy with Apple Mail’s

default text display, go here to change fonts
and point sizes. You can also change the
colors Apple Mail uses for displaying
quoted text in this screen.

173
THE VIEWING TAB

There are several options relating to how

Apple Mail displays messages, including
whether or not it displays images and how it
groups related messages together. This
screen also presents several options to
customize how Apple Mail displays images.

174
THE COMPOSING TAB

This screen has a list of useful options for

composing email. It lets you set the default
email message as rich text or plain text.
Settings for spell checking and addressing
new email messages are found here as well.
This screen also includes preferences for
email responses, such as whether or not to
include a quote of the text from the original
email message.

Apple Mail’s signatures and rules tabs are

already covered elsewhere in this book.

175
ADDITIONAL SETTINGS ON THE by default. You can also change the flag
IPHONE AND IPAD shape between a dot and a flag. If you’re
concerned about accidentally deleting an
On the iPad and iPhone, settings are
email, there’s a switch you can turn on that
accessed not in the Mail application but
will request
instead the Settings application. Tap on the Additional Mail Settings on the iPhone
permission
Mail, Contacts, Calendars button for the
before
mail settings. From here you can make
deletion. I
adjustments to your accounts and set your
would
accounts to push new email or have the
recommend
application fetch email on your schedule (or
this only if
when you open the Mail app). These topics
you have a
were covered earlier in this chapter.
low volume of
You can also adjust the number of lines Mail email,
uses to preview your messages. By default otherwise
Apple Mail previews two lines. I set mine at you’re going
four lines, which gives me a bit more to spend a lot
information and allows me to open less mail. of time
confirming
If you frequently use the carbon copy field, deletes. You
there’s a switch to allow you to leave that on can also
176
instruct Apple Mail to load remote images
(or not) and display email messages by
thread. Email threads allows you to see both
the email messages and the responses
directly related to it. I prefer viewing by
thread.

If you must retain a copy of your email,

there’s a way to send a blind copy of all of
your outgoing email to yourself. Here is also
where you can set up signatures and the
default email account used for sending
messages. Overall, there are quite a few
customization options for Apple Mail on the
iPad and iPhone. Spending five minutes to
adjust some of these settings will make your
email experience better suited for you.

177
 S E C T I O N 12

Apple Mail Automation

Another advantage of using Apple Mac to dragging and dropping

Mail is that it has pretty terrific prebuilt tasks on top of one
automation support. There is a another. Automator is
small team at Apple that spends something anybody can
its time thinking about pick up with just a little
automation on your Mac. These bit of effort. Moreover,
are the people that brought us Automator includes some
things such as AppleScript, really great tools for working
which allows you to use a in Apple Mail. Microsoft also
scripting language to give gets the value of automation and
your Mac commands, and has built several Automator actions
Automator, which reduces for use in Microsoft Outlook for the
automating tasks on your Mac.

178
 Automator Mail Actions
Let me share an example. Pretend activate an Automator-created
you are a salesperson and you go service that does all of the above
out on the road and you take for you in the background in a
notes at client meetings on your way that you don't even see
MacBook Air. Also imagine you Apple Mail open. I do this with
have an assistant that processes telephone messages at my work.
those notes for you. In order to Screencast 4.24 walks you
make that happen without through how I created the script
automation, you need open Apple and use it.
Mail, address a new message to
Looking at the list of available
your assistant, add a subject line,
commands for Apple Mail in
copy the information from your
Automator, there are a lot of
note-taking application and paste
options for you to automate your
it into the new email message,
own email workflows. Open
then add your signature and send.
Automator and take a good look
When you think about it, that is a
at these mail automation options.
lot of steps.
I'm betting that at least one of
With Automator you could simply them will be useful to you.
highlight the text in your note-
taking app right-click it and then

179
Screencast 4.24 Using Automator with Apple Mail

180
 S E C T I O N 13

Apple Mail for Mac Plug-ins

At this point, you are an Apple Mail pro. MAIL ACT-ON

You understand both the tactical and the
Note: As this book
technical pieces of making this application
goes to press, Mail
sing. Now it’s time to make it dance. A lot of
Act-On is not
people don’t realize that Apple Mail is
Mavericks
extensible. Third-party software developers
compatible. This
can write applications that plug into Apple
section was written
Mail, giving it additional features. Quite a
using the public beta
few of them have done so, and there are
(website) of the Mavericks version that the
several additional plug-ins to make Apple
developer intends to release for purchase by
Mail work even harder for you.
the end of November 2013.

Mail Act-On (website) simplifies the

process of managing incoming and outgoing

181
email. I explained earlier the ability to developer can bring to an application. It
automatically file email in different works with all of your mail accounts. It
mailboxes using keyboard shortcuts in includes the ability to undo rules you have
Apple Mail. That’s a relatively new native mistakenly applied with Command+Z. It
feature for Apple Mail. Until Apple added even lets you adjust exactly when the
this feature, Mail Act-On was mandatory to
streamline mail management. This plug-in Gallery 4.7
still exceeds the native Apple feature in
several ways.

For instance, Apple Mail’s rules only apply

to incoming messages. Mail Act-On expands
this to outgoing messages. So if you want to
automatically file outgoing messages to a
particular folder, this is the best way to pull
that off.

Mail Act-On’s developer, Indev Software, is

—in my opinion—the premier Apple Mail
plug-in developer. This plug-in has all the
nice subtle touches that an experienced

182
message gets marked as read so it doesn’t
screw up any of your other rules.

Mail Act-On is one of my favorite Apple

Mail plug-ins. Gallery 4.7 includes several
Mail Act-On screenshots.

183
MAILTAGS beginning. You can also
attach projects, importance,
Note: As this book goes to
and colors to your messages.
press, MailTags is not
It adds data to track due
Mavericks compatible. This
dates for emails and attach
section was written using the
them to events and tasks on
public beta (website) of the
your Mac. It is, in essence,
Mavericks version that the
a bowl of hot steaming
developer intends to release
metadata poured over
for purchase by the end of
your email.
November 2013.
This gives you all the
For a lot of people, the big selling
advantages of a traditional
point of Gmail is the ability to use
tagging system. It makes it easier to search
tags (called labels in Gmail) with
and locate specific emails. For instance, if
their email. (I explain this and Gmail in
you’ve tagged all emails related to a certain
further detail in chapter 5). However, if you
project with a specific project tag, getting
really want tags but also want to stay with a
access to that entire body of email is as
traditional IMAP server and Apple Mail,
simple as flipping the bit in MailTags for
you need MailTags (website). MailTags
that project tag. You can tag emails as they
allows you to attach keywords and tags to
arrive and as you write them so that all the
your email messages. That’s just the

184
email related to that specific project will MailTags, another product from Indev
show up. Software, is actively developed and
constantly taking advantage of the latest
The metadata MailTags creates will sync
improvements in the Mac operating system.
over an IMAP or Microsoft Exchange
The most recent version added the ability to
server so if you have multiple computers,
create notifications based on due dates you
you should get your data on all of them.
assigned to emails using MailTags. Another
great feature with MailTags is the ability to
Gallery 4.8 apply tags using Apple Mail’s rules. You can
automate email tagging and avoid some of
the overhead that comes with tagging. One
downside is that there is no way to sync the
tag information to Apple Mail for the iPad
and iPhone, so you won’t see the benefits of
your tags there.

A bigger question is whether or not you

want to spend time tagging your emails.
This depends on you. The search engines in
all the modern email clients are very
powerful. Using Apple Mail, I can easily

185
search for all email related to a certain interested in tagging email on the Mac, look
person in a certain date range that contain no further than MailTags.
keywords related to a specific project. But
all of that is dependent upon the right
criteria being contained in those search
terms. If someone writes me an email about
a specific project but never mentions the
name of the project, there’s a chance my
search won’t find it. If, on the other hand, I
use MailTags and tag every mail related to
that project with the project tag, I’m
guaranteed to see it. Of course that requires
me to take the extra step of tagging each
email I write and receive. That time adds up
so it becomes a cost-benefit analysis. If
investing that time saves you additional time
on the back end when you’re looking for
these emails, it’s worth it. If, on the other
hand, you rarely find yourself searching the
tags, then it’s time wasted. You have to
decide this one for yourself but if you are
186
 MAILHUB one sender or in a single thread. You can file
or delete all of the messages with one
MailHub (website) is
keystroke.
another top-tier Apple
Mail plug-in. My Like MailTags, MailHub also has options
favorite MailHub for email reminders, which show up in your
feature is predictive calendar. The reminders include the entire
filing. When I view a email, which is helpful. MailHub is best for
message with MailHub turned people who use multiple folders for sorting
on, the plug-in views the message and and storing email. If that’s you, you need
predicts where I will file it. If the MailHub.
application has it right, pressing Command
Gallery 4.9
+Enter files the message in that folder. If
MailHub gets it wrong, the application
makes it easy for me by pointing to an
alternative destination. MailHub also makes
suggestions for outgoing emails. If you
prefer to file your outgoing emails in
project-specific folders instead of a Sent
folder, this can be huge. MailHub simplifies
dealing with multiple email messages from

187
 CARGOLIFTER recipient’s mail server is going to reject the
mail, and you will, theoretically, get the
Sending email
message returned back to you. If that email
attachments
included important information, tough luck.
sometimes
This results in much gnashing of teeth every
feels a little bit
day.
like playing a
slot machine: CargoLifter (website) is an Apple Mail
you pull the plug-in that automatically uploads your
lever knowing email’s attachments to the cloud and adds a
you may or may link to the end of your email. Putting large
not get the result attachments in the cloud instead of
you want. Specifically, attempting to attach them to the email
email protocols were never makes a lot of sense. This plug-in does the—
designed to handle large attachments. excuse the pun—heavy lifting for you. The
Different mail servers have different recipient can download the files to wherever
attachment size limits. For some it’s 10MB, she wants on her computer, and you avoid
for others it may be much more (or much the risk of getting the email bounced or,
less). The point is when you send an email alternatively, flooding your recipient’s
to someone and you’ve got an attachment mailbox with unwanted attachments.
that is over that magic number, the Another advantage of this workflow is that

188
your PDF doesn’t get stored in someone
else’s unsecured email database.

CargoLifter supports several different cloud

services including Dropbox, Droplr, Gallery 4.10
CloudApp, and YouSendIt. If you’re a lone
wolf and you have your own FTP (File
Transfer Protocol), SMTP (Simple Mail
Transfer Protocol), or WebDAV (Web
Distributed Authoring and Versioning)
server, CargoLifter can work with those
too.Gallery 4.10 includes several
CargoLifter screenshots.

189
 FORGETMENOT Gallery 4.11

So here I am writing
a book about email,
like I know it all,
and during my day
job this afternoon, I
wrote a detailed email to
someone I wanted to impress.
I did everything right: I wrote it in the right
order. I used some spectacular words. I
printed out a hard copy and proofread it
with my big, red pen. Then I satisfyingly
clicked the Send button only to realize a
fraction of a second later that I did not included. If you want to appear professional
include the attachment. when you send an email and you say you’re
attaching a file, you probably should attach
Ugh.
the file.
After I managed to pry my stapler out of the
ForgetMeNot (website) is an application
drywall, I sat down, took a breath, and then
that watches your outgoing email for
sent an apologetic email with the attachment
keywords referring to attached files and
190
reminds you if there is not an attachment to
the email before sending it. It is already
loaded with predefined words, and you can
add more custom keywords yourself. It’s a
simple little app that solves one of the most
common email problems.

191
 ATTACHMENT TAMER One of Apple Mail’s features is the ability to
automatically resize images before sending.
Attachment Tamer
You can send an image in a small, medium,
(website) cures many of
large, or original form. I find this useful, but
Apple Mail’s sins when it
some people find it annoying. Attachment
comes to the subject of
attachments. Sometimes, Gallery 4.12
when sending
attachments to our Microsoft Windows
brethren, Apple Mail will include an
additional file called “ATT0001”. This is a
result of differences between the two
platforms. Attachment Tamer can send
messages compatible with Microsoft
Outlook/Exchange and other software,
preventing this problem. Also, Apple Mail
sometimes truncates the attachment names,
making it difficult to discern one from the
other. Attachment Tamer displays the full
attachment name.

192
Tamer has a setting to create a default size
for automatic image resizing. Attachment
Tamer also gives you more control over how
attachments appear in your email message.
You can specify, for instance, whether PDF
files show up as a preview of the document
or an icon. This is also true for text and
HTML files, images, and audio.

Somewhat related, if you want Apple Mail

to display attachments as files and not
display them inline, you can use a command
in the Apple Terminal:
defaults write com.apple.mail
DisableInlineAttachmentViewing -bool yes

193
MORE APPLE MAIL PLUG-INS MAILRECENT
There are a lot of email plug-ins for Apple MailRecent (website) adds “Copy to
Mail available. Here are some more: Recent” and “Move to Recent” options to
the Message menu.
FACE2FACE

Apple Mail relies upon your Contacts QUOTEFIX

database to attach photos to your email. If you took my advice about inline replies,
Face2Face (website) adds photos from your you may want to check out QuoteFix
Facebook and Gravatar accounts to the mix. (website). It positions the cursor below the
original message instead of above it.
FLAGGEDMAILS

This app (Mac App Store) puts access to SIGNATURE PROFILER

flagged email messages in your Mac’s Menu This plug-in (website) gives you even more
bar. control over Apple Mail’s Signature feature.

194
WINMAIL.DAT VIEWER

If you work with winmail.dat files,

Winmail.Dat Viewer (Mac App Store) can
save you from a lot of headaches.

195
 S E C T I O N 14

Apple Mail Platform Distinctions

Apple Mail is not iPad. Also, because the

created equal on the Mac has a lot more
Mac, iPad, and iPhone. storage than a mobile
Each platform has its device, the Mac can
own quirks and hold an entire email
advantages. The Mac archive.
version is best for
Email on mobile devices is more convenient
managing lots of email.
(you can answer email from anywhere) but
This isn’t just because of the Mac’s
also more limited. Apple has locked down
integrated keyboard. The Mac version has
the iOS operating system in ways that
the ability to run all of those plug-ins,
prohibit third-party applications from
AppleScripts, and other automation tools
working with Apple Mail. For example,
(such as TextExpander) that are not
TextExpander is a great email tool on the
available on Apple Mail for the iPhone and
Mac but unavailable in iOS Apple Mail.

196
Another challenge with iOS Apple Mail is
storage. A lot of us have gigabytes of email.
(My Mac currently reports my email library
is 14GB.) If you have a 16GB iPhone, you
don’t presumably want to use up 90% of
your storage with email. iOS Apple Mail
stores a limited amount of email on your
device and then resorts to the Internet-
stored version of your email for older mail.

Apple has made big strides with Apple Mail

such as keyboard shortcuts for filing and
organizing, VIPs, and a killer set of tools for
creating email rules. Moreover, a lot of these
features work across both the Mac and iOS
versions, which is extremely convenient.
Apple Mail is no longer something you just
live with but a powerful, extensible email
tool.

197
CHAPTER 5

GMAIL
 SECTION 1

Gmail

In chapter three I explained Several Gmail features just

how surprisingly old the don’t exist with traditional
POP and IMAP email IMAP mail services, and as
protocols are. When Google email power users, we must
decided to make its own email take note. Moreover, Gmail
product, its engineers took a is tightly integrated with
fresh look at email. Of course Google’s suite of utilities,
Gmail is innovative; it has the including calendaring, contact
backing of perhaps the best management, Google Drive cloud storage,
company on the planet at managing web- and Google Docs’ productivity tools. If you
based services and data. Gmail is much use Gmail, it makes using these other
more than a front end for an existing email services even easier.
protocol.
Because Gmail is web based, you can access
it through any Internet-connected computer

199
or mobile device. Another advantage of so much about you that it makes me wonder
Gmail is Google’s remarkable skill at where this stops being convenient and starts
managing lots of data. Google is full of getting creepy.
clever engineers who are constantly cooking
up ways to use those Google servers to THE CREEPY FACTOR
make email better. Google’s email servers
There is a real tired explanation about
don’t sleep, so all of the Gmail tools I’ll
Google and its products. Google doesn’t
cover in this chapter are working whether
charge you for Gmail and other services.
or not your computer is turned on.
Instead, it collects information about your
As this book goes to press, Google is habits and preferences and then uses that
developing its Google Now product. Google information to serve you advertisements that
Now looks at your email to identify your make sense for your preferences. So the way
flight information, view your calendar to Google makes money is selling ads, not
determine what time your flight takes off, charging you money to use Gmail or other
and sends a notification to your phone Google services. The point is you’re not
letting you know what time you should paying for Gmail because Gmail is not the
leave, how traffic looks, and otherwise Google product—the Google product is you.
provide useful assistance. All of this is The more Google knows about you, the
possible because of the combination of better ads it can sell, and the more money it
Google services. Indeed, Google can learn makes.

200
As consumers, we need to go into this with about how your septic tank recently blew up
open eyes. I don’t think there is a room at in a neighborhood apocalypse, there’s a
Google where people open your email and good chance you will see ads for septic tanks
read your personal correspondence while on the page. For most people, this isn’t a
eating a bacon-wrapped meatloaf sandwich, problem. Indeed, it can be a convenient
but I do think there are computers that are advantage. Quite often the reason you write
constantly scrubbing your Gmail data to about specific products is because you are
look for keywords and terms that tie to looking to purchase them. If your email can
products they can advertise to you. Don’t point you to someone selling the product, all
believe me? Look at the sidebar in your the better. For other people, it’s just too
Gmail web client. If you write your friend much. I don’t think there is a right or wrong
Google Terms as of November 2013

201
answer as to whether or not you use Gmail. are talking about so it can serve her better
I wouldn’t use a free Gmail account for ads. I haven’t agreed to allow Google to do
confidential emails. I do use it for my that. Indeed there is litigation against
podcast account (and used it for quite a bit Google on this point as this book goes to
more email while writing this book). I’m a press. Gmail is so entrenched at this point
little creeped out about how much that I suspect Gmail is not going to change
information Google collects on me. I'm not any time soon.
so creeped out that I think nobody should
Google has a paid email service for
use Gmail but enough so that I think all
companies called Google Apps for Business.
users should understand how Gmail works.
This provides users more privacy, according
Moreover, I also think the concept of
to Google (website). If you want the benefit
privacy is in flux, and people increasingly
of Gmail but are concerned about privacy,
just don’t care that Google scrubs their
consider setting up a Google Apps account
emails to serve ads.
to avoid this problem. Either way, there is
There is another angle to this problem: what most certainly an eroding sense of privacy
about people who are not Gmail users but as technology becomes a bigger part of our
correspond with Gmail users? When I send lives. Companies such as Google and
an email to my friend through her Gmail Facebook clearly fall on the side of this
account, Google is also presumably reading argument that the loss of privacy is worth it
my message to get a better idea of what we in exchange for the benefits that arise from

202
these companies having access to your data.
Companies such as Apple and other private
IMAP mail servers work on a more
traditional model: they aren’t serving you
ads but instead taking your money (either
through IMAP subscription or as part of
hardware sales) to provide you an email
service. There isn’t an easy answer to this
question, and I'm not going to spend a lot of
time navel-gazing about it in this book.
Everyone has to make their own decision
and should do so with open eyes.

If you do decide to use Gmail, there are

some pretty great things you can do with it.
This chapter will demonstrate my favorite
Gmail features and workflows.

203
 SECTION 2

Email in Your Browser

Gmail is the ultimate web- Google experience and, in

based email service. some ways, better.
Naturally, it is built around
Even though Gmail is in a
managing email from your
web browser, in some ways it
web browser. If you’ve spent
feels a lot more like an
years working in an email
application: It has keyboard
application, this is going to
shortcuts. It has special and
take a little getting used to.
unique features. It has a
Indeed, there are several
settings screen. In other ways,
third-party apps that are
it still very much feels like a website. In my
designed for Gmail, but if you’re switching
opinion, despite the work of many talented
to Gmail, I recommend starting in the
Google engineers, email on the web still
browser. This is uniquely suited to the
does not feel as natural as email in a native
application.

204
 SECTION 3

Setting Up a Gmail Account

getting a username usually takes a few

attempts. Once you’ve got your account set
up you’ll get to the actual Gmail interface.

The left side of your screen lists your

To create a new Gmail account, go to mailboxes, labels (explained later), and
Gmail.com and click Create an Account, online social contacts. To find the links to
which is located in a blue box in the upper- other Google services such as Google+,
right corner. You will be directed to YouTube, Maps, Drive, Calendar, and more,
complete a a series of dialog boxes click the Apps grid to the right of the Search
prompting you for details such as your bar at the top of the screen. The rest of the
name, username, password, and other screen is used for some interface buttons
information. It might take a few minutes. Be and to display your messages.
warned that Google is extraordinarily
popular so unless you have a unique name,

205
 The Standard Gmail Interface in the Safari Browser

Settings are found by clicking the Gear icon opinion, hideous. It had bad colors and bad
on the right side of the screen, which is typography, and it looked like something
where you will manage and enable all the that had 99% engineering and 1% graphic
Gmail features covered in this chapter. You design. It was a running joke that Google
can also adjust the density of information made fast, efficient, ugly web experiences.
provided on the Gmail site with the That isn’t true anymore. Google has clearly
Comfortable, Cozy, and Compact settings. worked on design a lot, and Gmail is a much
Traditionally, the Gmail interface was, in my more pleasant experience than it used to be.

206
One useful feature for people transitioning
to Gmail is the ability to pull email from
other email accounts into Gmail for you. If
you are moving from a cable company email
to Gmail, for instance, this is helpful. To do
so go to the Gmail Settings screen and click
Settings→Accounts→Check mail from
other accounts (using POP3):. Gmail will
ask for your account credentials and take
care of the rest. You can even
send email from within Gmail
that appears as if it is coming
from your old account, if you
like.

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 SECTION 4

Gmail Inbox Categories

In most email applications and services, an you’ll see 12 Primary messages with tabs
inbox is just that: a single place where all including another 30 messages roughly
new emails collect. Google has a filtering sorted for you. This is similar to the
algorithm that it applies to your inbox for SaneBox service covered in chapter 3. It
you, separating categories of mail. By comes free with a Gmail account and works
default these include Primary, Social, and pretty well. This doesn’t give you the same
Promotions tabs. If, for instance, an email degree of control as SaneBox, nor does it
comes in from LARP-U, your favorite give you all of the same features, but it is
LARP (Wikipedia) costume store, it will go free with every Gmail account and solves
in the Promotions tab and not clutter up the problem of a large, unsorted inbox.
your inbox. There are additional categories Screencast 5.1 demonstrates Gmail Inbox
for updates and forums. Categories.

The benefit is when you look at your inbox,

you won’t see a list of 42 messages. Instead,

208
Screencast 5.1 Gmail Inbox Categories

209
 SECTION 5

Gmail Keyboard Shortcuts

GMAIL LOVES THE KEYBOARD that users often forget. In Apple Mail, for
instance, you need to hold down three
Keyboard shortcuts often make the
separate keys, Command+Shift+D, to send
difference between getting your inbox
an email. For me at this point, it’s second
cleared in 20 minutes or five minutes. It is so
nature because I’ve been doing it for so
much faster to keep your hands on the
long, but for a lot of people it’s pretty
keyboard as you’re working through your
difficult to remember something so intricate
email. The trouble with most email
for something as simple as sending an email.
applications is that keyboard shortcuts
In Gmail, this takes just two key presses,
involve complicated combinations of keys

210
Command+Enter, which makes a lot more in the Gmail Settings tab. Don’t forget to
sense. save the settings after turning them on.

That’s not all. Command+N is used to Here’s a list of some of my favorite keyboard
compose a new message in Apple Mail. In shortcuts in Gmail. For more, check out
Gmail, it is just one key: C. Gmail does Google’s handy list (website).
keyboard shortcuts better, which is kind of
C to compose a new message.
surprising. You’d think that doing keyboard
shortcuts in a web browser would be more R to reply to current email.
difficult to implement than in native
applications. Whatever the reason, pressing F to forward current email.
one key instead of two (or three) to trigger a J to go to the next email.
keyboard shortcut is easier to learn,
remember, and use. Because these keyboard K to go to the previous email.
shortcuts are so easy to trigger, Google
L to open the label menu.
makes you turn them on. They don’t want
users accidentally deleting, archiving, or . (Period) to activate the More actions
moving their emails without realizing what drop-down menu.
they’re up to. Turn on the keyboard
shortcuts in General→Keyboard shortcuts: Y does many things. Its point is to remove a
message from wherever you are at.

211
• From Inbox, pressing Y after selecting YO to archive the current email message
conversations will archive them. and move to the next one.

• From Starred, pressing Y after selecting GC to display your Google contacts.

conversations will unstar them.
GD to display your draft emails.
• From Trash, pressing Y after selecting
conversations will archive them.
Screencast 5.2 Gmail Keyboard Shortcuts
• From any label, pressing Y after selecting
conversations will remove the label.

• It has no effect if you’re in Spam, Sent

Mail, or All Mail.

GA to display all Gmail you’ve ever sent or

received.

# to delete current email.

GT to display Sent mail.

D to compose a new message in a new tab.

212
CONVERSATION-VIEW SHORTCUTS L to open the Labels menu to label a
conversation.
Google was one of the pioneers in the
practice of displaying your messages in Shift+U to mark message as unread.
relation to one another, sometimes called a
threaded conversation. If you look at an email Command+S to save current email as a
from your friend, for instance, you will see draft.
your prior email in the chain displayed right You really have to see the keyboard
below. Google calls this Conversation View shortcuts in action to appreciate how fast
and it’s hugely beneficial. There are they are. That’s why I made screencast 5.2.
keyboard shortcuts that will allow you to
navigate while in Conversation View. If, even after all of this, you want further
help with Gmail keyboard shortcuts, check
N to move your cursor to the newer out the KeyRocket for Gmail Chrome
message. extension. (website)
P to move your cursor to the older message.

E to archive current email.

A to reply all.

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 SECTION 6

Searching Gmail

The reason for Google’s incredible success is continued to hold this commanding lead in
its search algorithm. Google was the first search technology ever since.
company to figure out search and upon that
The basic search in Gmail is usually all you
technology, they’ve built their entire
will need. Gmail
company. I
does a great job
remember the
of quickly
first time I used
finding your
Google search, I
results as you
thought they
type in your
must be using
search. If you
alien technologies. Google search was so
need to drill even deeper, you can use
much better than its competitors at the time
modifiers. For example, let’s say you and I
that there was simply no contest. They’ve
have 4,200 emails between us. (We are really
close friends.) You want to look for that

214
message from me concerning your pet, a the tools in Gmail (many of which are
white-faced capuchin monkey named discussed below) to help refine your search.
Dreyfus. You could type the following For instance, you can include operators for
search: whether or not the message is starred
(is:starred) or even starred with a
David Sparks subject:Dreyfus
specific color (has:red-star). You can
You could also replace David Sparks limit the query to messages that are marked
with from:david@macsparky.com. important (is:important), have an
Google supports several of these operators attachment (has:attachment), have
including Subject:, From:, To:, CC:, and been read (is:read), or based upon the
BCC:. Note that the operator is always message date (after:2012/12/18). You
followed by a colon (:) and immediately can also modify search terms.
followed by the operator subject. (There are
Placing search terms in quotations
no spaces.) Google goes far beyond these
(”Dreyfus’s diaper”) looks for an
basic operators. They take advantage of all

215
exact phrase. Adding the plus sign (+) to the While I’m not a big fan of spending a lot of
beginning of a word looks for that exact time organizing your emails into specific
version of the word and not any alternate message folders, I am a huge fan of power
versions. For instance, +bananas will not searching your email. If you’ve taken my
return the word banana. Adding the minus advice and put most of your emails in a big
sign (-) to a word excludes any emails archive, spend some time getting to know
including that word from the search. For how to search your email application so you
example, subject:Dreyfus -banana can get to what you need faster. Gmail leads
will return emails that have the word Dreyfus the way on this but not as decisively as they
in the subject line but not the word banana. used to. Apple Mail also has some very
Google keeps an updated list of its Gmail powerful search tools, which were explained
search terms online (website). earlier in chapter 4.

Once you get good at crafting Gmail

searches, you can use the search terms to
also create Gmail filters, covered later in
this chapter. As boring as this all probably
sounds, it is a smart investment of your time
to get really good at Gmail search.

216
 SECTION 7

Gmail Labels

Labels are one of placing multiple

Gmail’s most copies of the email in
compelling features. multiple folders but
Gmail labels are, in instead giving it
essence, tags. For multiple labels. A
instance, an email labeling system could
from a customer could let you organize and
have labels for see your email in
specific products, the multiple ways. As
Assigning Gmail Labels
customer’s company, another example, let’s
product release say you buy a privacy
cycles, and other criteria that make sense for scarf (website). You could label the email in
it. Unlike IMAP mailboxes, you can apply Gmail with receipt, clothing, taxes, and work
multiple labels to a single email. This is not expense labels. You could later search just for

217
emails with the receipt label and your privacy email client. They simply don’t know how to
scarf receipt email would be right there. I process labels and often mistake them for
know a lot of Gmail users have software IMAP-type mailboxes. The problem is,
license labels so every time they buy a new however, IMAP email messages don’t go
piece of software, they can label the into multiple folders, but Gmail messages
confirming email with the software license can have multiple labels.
and easily find it later. By using Gmail
filters, explained later in this chapter, you
Screencast 5.3 Gmail Labels
can automatically assign labels, which gives
you the benefit of their organization without
the expense of their creation.

Gmail labels appear in the left sidebar of

your Gmail window. If you create too many
and the sidebar starts getting cluttered, you
can organize these and even hide certain
labels in the Settings window in the Gmail
application.

Labels are one of the reasons why Gmail

often has trouble working in a traditional

218
Some applications resolve this problem by
making and filing multiple copies of the
email, and others seem to randomly pick one
of the labels. The best solution is to use an
application that is designed specifically for
Gmail and its labels. I will point out a few of
the best applications later in this chapter.

Screencast 5.3 demonstrates how to create,

search, and organize Gmail labels.

219
 SECTION 8

Server-Side Filtering

As you’ve probably always checking your

already figured out mail anyway for spam
from prior chapters, filtering and to serve you
I’m a big fan of email ads, it has some really
filtering. The more our powerful tools for
email application can autosorting, filtering,
manage email for us, and managing your
the less time we spend email.
dealing with the
Moreover, because this is
nonsense and the more Creating a Gmail Filter
done on Google servers,
time we spend with
you don’t need to have a
the substantive email. Gmail is particularly
computer plugged in for this work to take
good at this. Because your mail is hosted on
place. As much as I like Apple Mail’s rules,
their web servers and their web servers are
which are even more powerful than Gmail’s

220
server-based rules, Apple Mail’s rules only needs the rule, and (2) do something to the
works if Apple Mail is running on a Mac email.
somewhere. I know
In checking mail for
some users who
application of a
keep a Mac running
filter, Gmail looks at
at their home all the
the sender,
time for the sole
recipient, and
purpose of running
subject line, similar
Apple Mail rules.
to iCloud’s server-
You wouldn’t need
side filters. Gmail
that with Gmail. In
also can search the
addition, Gmail’s
contents of the
online mail rules are
message for words
more powerful than
that are (or are not)
those offered by
there. The ability to
iCloud and other
Available Actions for Filtered Email look inside the
similar services.
message for filter
Similar to Apple Mail’s rules, there are two creation gives Gmail filters the edge over
pieces to a filter: (1) determine which email iCloud. Gmail also lets you look at more
than one criterion. I could look for messages

221
from Katie that don’t include the term With a set of rules, Gmail could take much
Batliff. In iCloud server-side filtering, I can’t of the drudgery out of managing your email.
combine both of those into a single search. I use these rules extensively in my Gmail
Apple Mail’s rules are better, but they are accounts and always wish I had them on my
done locally and, again, require a Mac to be other email accounts. Screencast 5.4
plugged in somewhere. demonstrates creating and using Gmail
filters to manage email for you.
Once I’ve selected an email through this
filtering, Gmail gives me several options for Screencast 5.4 Gmail Server-Side Filtering
what to do with it. I can archive the
message, mark it as read, star it, apply a
specific label to the email, or forward it to a
specific person. I can also delete the
message or mark it as spam. Likewise, I
could mark the email important so Gmail
knows where to categorize it when I receive
similar emails in the future. All of this is
done online by Gmail as soon as the email
shows up.

222
 SECTION 9

Gmail Stars

Gmail stars are similar to Apple Mail flags cycle through the available stars, just keep
but with more features. Gmail stars include tapping on the star. While I appreciate the
different colored stars and little icons such expanded usage of multiple stars and icons,
as checkboxes, exclamation points, every time I’ve tried to use them in Gmail I
questions marks, and other symbols. To eventually gave up on them. To go through

Setting Up Additional Stars in Gmail

223
and apply the various stars seemed more
trouble than it was worth. This might just be
me since I also barely use flags in Apple
Mail. It may also be because I aggressively
Gallery 5.1
use labels whenever I use Gmail and have
already created label versions of most of the
star symbols. As an example, I have a
“Needs Reply” label. I’m not sure this is a
knock against Gmail stars so much as an
endorsement of the various ways you can
mark an email in Gmail as special. If stars
make more sense to you than labels, go for
it.
This email is using a green check mark
To add additional stars and related icons in as its star. It is displayed to the right of
Gmail, go to the General tab in Settings and the recipient’s name.
scroll down to Stars and drag any stars you
want to the in use row. Gallery 5.1
demonstrates Gmail stars.

224
 S E C T I O N 10

Google Labs

In the Gmail Settings page there is a tab for

Labs. This is the place where Google tries
out new Gmail features. For example,
they’ve got one Lab feature that lets you
undo sending an email in the first few
seconds after you send it. There is another
Lab feature that lets you create canned
email responses and send them without
retyping. Others are more mundane, letting
you further customize the interface. The
Lab feature list is always changing and
experiments appear and disappear, but if
you use Gmail you should be checking this
out regularly.
Google Labs

225
 S E C T I O N 11

Third-Party Apps for Gmail

APPLE MAIL treating it, more or less, like an IMAP

client, Apple Mail is an option. When OS X
While there is a lot to like
10.9 Mavericks first released, Apple Mail
about Apple Mail, it is not a
became even less useful as a Gmail client.
very good Gmail client. It
However, Apple did issue an update to make
isn’t built around Gmail and
Apple Mail more Gmail-friendly.
it shows. You simply don’t
get all of the Gmail features listed in this I still think, though, that if you want to get
chapter using Apple Mail. the most out of Gmail, you should use an
email client that embraces all of the Gmail
Nevertheless, a remarkable number of
features. That is not Apple Mail. There are,
Gmail users use Apple Mail to run their
however, some good alternatives.
Gmail accounts. It makes sense if you also
have non Gmail accounts and don’t want to
use multiple email clients. If you are just
using the basic features of Gmail and
226
 MAILTAB PRO and the application also supports Google
Talk. In addition to the drop-down menu
MailTab Pro (Mac
bar, you can also expand it for the full Gmail
App Store) puts
experience with its own screen.
your Gmail inbox
in your Mac’s You can activate MailTab Pro with a
Menu bar. From keyboard shortcut (Control+G). There is
there you can quickly also a keyboard shortcut to open the
check your mail without compose window (Shift+Command+M)
going to the browser. There are that I find really useful.
notifications available (if you go for that),

MailTab Pro Screenshot

227
 MAILPLANE FOR If you want a native Mac app for your
THE MAC Gmail instead of the browser, I recommend
Mailplane. Mailplane (website) is a Mac
On my Mac I
app designed around giving you a native
prefer to run
application for Gmail. It is currently
Gmail from the
shipping a third version and includes
browser. It really is
support for many Gmail features. It
how Google intends
integrates with Google Calendar, supports
you to use this
up to 10 separate Gmail accounts, allows
service and, despite
you to switch between them with tabs, and
the drawbacks of being in a browser, I
automatically uploads attachments to drop
still think it is the superior experience for
into the application to Gmail. It supports
managing Gmail.
Macs with Retina display and even includes
If you were thinking about using Apple support for plug-ins (including AwayFind
Mail instead, don’t. Apple Mail does work [website], covered in chapter 3).
with Gmail, but it feels like a square peg in a
round hole. The problem is Apple Mail
simply wasn’t designed for some of Gmail’s
more innovative features, such as inbox
filtering, multiple colored stars, and labels.

228
The experience of using Mailplane isn’t all
that different from using Gmail in the
browser. Tapping the Mailplane icon in your
toolbar opens a browser-like window with
your Gmail account, as shown in the Mailplane for Gmail

accompanying screenshot. I know a lot of

Gmail power users who swear by Mailplane.

229
GMAIL APP FOR IOS on the iPad and iPhone, I wouldn’t think
twice about the decision to use the Gmail
Apple Mail for iOS
app. It’s free and I demonstrate it in
supports Gmail accounts
screencast 5.5.
right out of the box.
However, the Gmail app
from Google does a
much better job with
Gmail.
Screencast 5.5 The Gmail iOS App

Using the Gmail app, you can get those

instant notifications (even customized to
specific mailboxes) and take advantage of
various Gmail services such as inbox
categories, labels, stars, and other features
that don’t work in the Apple’s Mail app. In
my opinion, the iOS Gmail application is
also more attractive than the web-browser
version of Gmail. Google has traditionally
had a reputation for not making particularly
attractive applications, but I think the iOS
Gmail app disproves that. For use of Gmail

230
 S E C T I O N 12

Should You Use Gmail?

For a long time I was pretty Google using your data to perfect
judgmental about Gmail. The fact its ever-growing advertisement-
that they use the contents of my serving machine.
email to serve ads was just a non-
I explain further in my own
starter for me. Over the years
workflow at the end of the book
however, my own expectation of
that after letting go of my Gmail
online privacy has eroded and
hangups and using it for a few
Gmail has become even more
months while researching this book,
useful with some really compelling
I very nearly started using Gmail
features. I no longer think it is a
full time for my own personal email.
bad idea to use Gmail, but I do think
potential Gmail users should go in with In answer to the above question, I think
open eyes. Understand you’re getting a Gmail is a good service. If you decide to use
pretty great email service in exchange for Gmail, you should use it entirely with all of

231
its experimental features and innovations.
What I mean is that if you are going to go in
with Gmail and let Google collect your
information, take advantage of all of the
features so you get something in return. If
you aren’t going to use Gmail’s best features,
you’re better off opting-out and setting up a
traditional IMAP account.

232
 CHAPTER 6

MORE EMAIL
CLIENTS
When email first became a “thing”, there intentioned developers have begun releasing
was a healthy competition among software email applications to the market for the
developers to win your dollars with their Mac, iPad, and iPhone.
email clients. Somewhere along the
I attribute this to the fact that
way, however, operating system
people are realizing that email is
manufacturers, such as
increasingly difficult to
Microsoft and Apple, began
manage and they are
shipping email clients with
looking for solutions. We
a built-in operating
aren’t just looking for an
system. Suddenly
application that checks
everybody had a
all boxes and supports
competent email program
IMAP, Google, or
that was free. This
whatever your email
decimated the market for
choice is. Instead, we’re
third-party email clients and
looking at applications to
for a very long time there
help us manage email better.
simply was no competition to the
free built-in options. In this environment, we just aren’t
getting big full-fledged email replacements.
That, however, is changing. Over the last
We are also getting little speciality email
few years, several well-funded and well-

234
apps that just solve one problem really well
and the full knowledge that you’ll be
managing at least some portion of your
email in a different application.

The good news is that suddenly there is an

influx of new third-party email applications,
and a healthy competition exists. Innovative
solutions to email can make our lives easier,
and it seems people are finally swinging at
this problem. This chapter points out a few
of the most interesting third-party email
solutions.

235
 SECTION 1

Mac Email Clients

MICROSOFT OUTLOOK Outlook (website) is Microsoft’s email,

contact management, task management, and
For a long time there
calendar application. This is Microsoft’s
was this bizarre holy
interpretation of the be-all and end-all
war between Microsoft
application for Exchange users. Outlook
and Apple users. What
works with Exchange Server 2007 or later.
a lot of Mac users
In late 2014, Microsoft released an update
didn’t realize is that there is a
for Outlook (the prior version was 2011).
contingent of rabid Mac users inside
Interestingly, this was the only All of that
Microsoft who love their Macs and spend
said, Outlook works just fine with
every waking moment trying to make
traditional IMAP and POP accounts.
Microsoft Office for Mac a uniquely Mac
experience while still retaining compatibility Outlook’s predecessor, Microsoft
with its Windows cousin. Entourage, had several quirks (including a
single database for all of your email,

236
contacts, and calendars, which, if it got corrupted or trashed, your data remains and
corrupted, may have led users to commit Outlook simply rebuilds the database.
physical violence against their Macs) that
When it comes to reading and writing email,
kept me from recommending it to anyone.
Outlook delivers. It includes the features
Outlook is much better. It does have a
we’ve come to expect. Custom signatures
database file but if the database file gets
Gallery 6.1

237
and address and calendar integration are all In terms of automation, Microsoft has
in the single application. Outlook goes always been good about including support
above and beyond with email rules, giving for AppleScript and Automator. If you want
users a similar experience to Apple Mail’s to automate email using these tools, you’ll be
many ways to analyze incoming email and fine with Outlook.
perform specific tasks on them. The
The real use case for Outlook is if you are
application uses Microsoft’s ribbon
deep in a Microsoft Exchange network.
interface, which a lot of people complain
Even though Apple Mail includes Exchange
about. I don’t think it is that bad. I would,
support, Microsoft’s Outlook goes deeper
however, prefer that power users could give
with Exchange features and support. Where
more customization to the ribbons so that
Apple Mail includes Exchange support for
the features we need most are available and
the convenience of its users, Outlook was
others we don’t use can be sent away.
built around Exchange support. Many (but
Outlook is also more stable and, in my not all) of the features from Outlook on
experience, faster than its predecessor Windows make it over to the Mac in
Entourage. Put simply, it feels a lot more Outlook 2014 for Mac.
like a Mac app. If you have attachments in
This book is not going to cover the calendar,
an email message, selecting it and tapping
task management, and contact capabilities of
the space bar gives you a quick look, like
Outlook except to say that they are there
the rest of OS X.

238
and a workable solution, particularly for
users on Exchange networks.

239
 POSTBOX link from Dropbox and add it to the
message.
Postbox (website) is
probably the most Like Apple Mail and Gmail, Postbox
popular third-party supports the inclusion of conversations and
replacement for threaded email discussions. Postbox will
Apple Mail. It look through multiple folders to put these
doesn’t try to copy together and makes it easy for you to track
Apple Mail but an entire email conversation. I also like the
instead goes a clever way Postbox handles replies. Postbox
different direction. One of its premier has the ability to create a reply without
features is the ability to automatically link opening a separate compose window. This
large files from your Dropbox (website) lets you view the source message at the top
account into the body of an email message. of the screen and reply at the bottom.
Simply drag the file from Dropbox into the Alternatively, the compose window has a
body of your Postbox message, and it feature called Summarize that cleans up
creates a link. The recipients can then messy email threads and then replaces them
download the Dropbox file by clicking the with a digest of who said what. When
link. This is also possible in Apple Mail, but composing a new message, you can use the
it’s not as easy. Instead, you need to get the search tool to find files for attaching to your

240
email without having to leave the compose same keyboard shortcuts that you get with
window. the native Gmail client. If you want to use

Postbox also includes support for Evernote

(website). The connectivity between Gallery 6.2

Evernote and Postbox is impressive. You

can automatically use the message subject as
a title and apply Evernote tags. Also,
message attachments are sent over to
Evernote and a direct link is created so you
can go straight back to Postbox from
Evernote to the source message.

While in the end I think Mailplane is the go-

to application for Gmail, Postbox’s Gmail
support is not shabby. It works with Gmail
labels and even has a dedicated Important This is a sample of the way Postbox will
view that shows Gmail-identified high- summarize a conversation for reply.
priority messages. Postbox can also detect
dates in your Gmail messages and add them
to your calendar. Finally, it uses all of the

241
Gmail in addition to other IMAP accounts,
Postbox does a good job at managing both.

Postbox also has its own tagging support.

You can assign a message to a particular tag,
and it is applied to all the other messages in
the conversation. This works with Gmail or
any other standard email account in
Postbox. There is a version of Postbox for
Microsoft Windows, if that’s your thing. If
you are a Microsoft Exchange user, move
along. Postbox does not support Exchange
email.

I spent significant time using Postbox in

preparation for this book and was more
impressed than I expected to be. It really is
nice seeing that third-party mail application
developers are bringing some innovative
solutions to email.

242
 MAILMATE exception. MailMate’s does render HTML
in incoming mail.
MailMate (website) is
an IMAP and Gmail So why on earth would you ever want to use
email client. If you use this application? For one reason, it’s fast.
Microsoft Exchange or Because it is largely working in plain text,
Gmail (or even POP), it messages display and can be composed very
won’t work for you. The quickly. Also, MailMate has some very
interface is entirely text. As powerful search criteria. Where most email
far as I can tell, there is not a single icon in applications limit search criteria to things
the entire application. There isn’t even any such as the recipient and sender, MailMate
formatting in the application for composing goes completely crazy with this. You can
emails. This application writes email in plain search for a single word embedded inside
text. (There is an exception if you know the email header. You can search for quoted
how to write in Markdown and if you don’t, or unquoted text. Forensic computer
there is a MacSparky Field Guide on researchers who need to look through vast
Markdown [iBooks Store] to fix you up.) bodies of email for that one smoking gun
For some people the plain text is a selling would absolutely love the search tools
point. I’ve spent plenty of time talking to available in MailMate.
people about the merits of plain text
(website) in any medium and email is no

243
 MailMate has been getting a lot of
Gallery 6.3
development love recently and they are
funding a new version 2.0 which promises to
keep that same under-the-hood power but
also add a better interface. MailMate could
come out of this next update as the go-to
application for Mac power users.

In version 1.0 of this book, I had a great

analogy of MailMate to a 1970s-era Buick:
MailMate isn’t very pretty but man does it
have a lot of power under the hood.
However, that analogy seems to be falling
apart.

244
 AIRMAIL There are built-in filters to show, for
instance, all messages with attachments. In
Airmail (Mac App
that case, you just tap on the Paper Clip
Store) (website)
icon. It also supports conversation view and
is another up-
lets you organize by subject or person.
and-coming
third-party Mac
mail client.
Airmail supports Gallery 6.4
Gmail, iCloud, Yahoo,
AOL, and generic IMAP clients. There is no
Microsoft Exchange support.

For a third-party, independent application,

Airmail’s got a lot under the hood. The user
interface is very attractive and immediately
useable. I found it very easy to manage my
email from inside Airmail and really like the
little touches, including the very satisfying
sound effects as I worked through my mail.

245
Airmail includes great support for keyboard
shortcuts (including Gmail shortcuts) and
even lets you write your email using
Markdown, which always makes me happy.

While it is still early days, AirMail is an

application that I could see myself someday
using full time.

246
 UNIBOX
Gallery 6.5

Unibox (Mac App

Store) (website)
takes an entirely
different approach
to email. Instead of
organizing your
email chronologically, it
organizes your email based on your
contacts. Once you set up Unibox, you will
see a list of your contacts on the left side of
the page. If your contacts have photographs
in your Contacts app on your Mac, that
picture will show up in the mail application. While I like the idea of a different way to
Clicking on the contact displays a list of organize email, Unibox wasn’t practical with
messages with that contact. the large volume of email I manage. As this
book goes to press, Unibox is new and I’m
There are some other innovative features in
keeping the app on my Mac to see where the
Unibox. For example, you can see a list of
developers go with it.
all attachments exchanged between you and
another person.

247
 SECTION 2

iOS Email Clients

MAIL PILOT Rather than fight the inclination to turn

your inbox into a task list, Mail Pilot (iOS
One of the
App Store) (website) embraces it. Mail Pilot
underlying
is a mail application for the iPad and iPhone
themes of this
(with a Mac app on the way) that
book is that your
incorporates task management into your
email inbox is not
mailbox. When a mail message arrives in
your task list.
Mail Pilot, you can archive it, file it away
Your inbox is ill-
with the project, or even file it away for a
suited for this
specific future date. It allows you to defer an
purpose and ends up costing you a lot of
incoming email so you don’t see it for a
time and making you act like a flake. Mail
certain number of days.
Pilot’s developers attempt to turn this fact
on its head. Say your coworker asks you to return his
Brony T-shirt (Wikipedia) at the staff

248
Gallery 6.6 meeting next Wednesday. You could push the email back
so you don’t see it until then.

In order to make all of this happen, Mail Pilot is required

to add several mailboxes to your IMAP account and
constantly communicates with servers to make sure it
keeps up with what email it should display and which it
should hide.

There is a growing movement of apps giving you the

ability to defer email to some future date. Mail Pilot is
probably the best of them. If you find yourself constantly
overstuffing your Action box, deferred mail is not a bad
idea. I’ve started using deferred email in some instances
but I do it through the SaneBox service.

249
 DISPATCH of different ways to put that message
somewhere else. As I write these words,
As you’ve read
there are 16 different available actions for
throughout this
an email message ranging from copying the
book, I’m a big fan
message to your clipboard to inserting them
of letting the robots
into some other application, such as
in our electronics
Evernote, OmniFocus, Fantastical, or a big
take the tedium out
list of others. If you’ve got a preferred
of email management
“thing” you like to do with your email
for us. One aspect of
messages outside of the email application of
this is getting information out of email and
choice, Dispatch streamlines the process of
into applications where it is better suited.
getting it there.
This is more challenging on the iPhone and
iPad because iOS doesn’t make it as easy to Dispatch also gives you a lot of options for
share data between apps as the Mac OS other formats of data. For web links, you
does. This is the problem that Dispatch can open them in any one of a variety of
(iOS App Store) (website), an iPhone-only supported iOS browsers (such as Safari,
mail application, attempts to solve. Chrome, and others), you can send the link
to 1Password, or you can read it later on
Dispatch focusses on action-based email
services such as Pocket (website) or
management. When you select an email
Instapaper (website). The application also
message in Dispatch, the app gives you a lot

250
gives you multiple app destinations for dates and times, Gallery 6.7

phone numbers, emails, and addresses.

There is a Quick Action bar across the bottom of a message

from where you can perform a variety of actions on an
email including marking it as read, flagging the message,
archiving it, filing it in a different folder, or deleting it. In
Settings you can assign a specific folder to Quick Move.
When you do that by tapping and holding on the Down
Arrow in the Quick Action menu and dragging it to the left,
it sends the email to the folder without requiring you to
navigate a folder list. I use this for my Action folder and it
helps me make quick work of the inbox. If you drag the
Quick Action bar further, you can immediately archive a
message. (There is also an Undo button that briefly appears
so you can fix any mistakes.)

Once you open a message, there is an Action icon that

enables you to invoke all of the sharing features I covered
above. The interface for this is nice, showing just icons for
the applications you’ve turned on. Tap on an icon and the

251
message gets delivered to the third-party its own built-in text snippet feature. The
application. For a lot of applications this implementation lets you search your
means you’ll get taken out of Dispatch and snippets as you use them, which is nice.
taken into the third-party app for additional
Dispatch has its own search tools. You can
processing, which throws some people off.
narrow your search to specific fields
One really clever feature is an automatic including the sender, recipient, subject line,
salutation. When you reply to a message, and message contents. Dispatch supports
Dispatch starts the email for you. If, for multiple email protocols such as IMAP,
instance, I’m replying to an email from Gmail, iCloud, Yahoo, and even AOL.
Kourosh, the email starts Hi Kourosh. It
While Dispatch really isn’t the full-fledged
grabs the first name from the source email
email client you would want to use to
and automatically inserts it. You can turn
replace something such as Apple Mail or the
this off, but I really dig it. It makes replying
Gmail application, it is a powerful tool for
to email just a little bit easier. Also, because
helping you manage an active inbox and it
I often use Siri Dictation for email replies, I
gives you features that simply aren’t
don’t have to worry about Siri choking on
available in the more full-fledged email
my correspondent’s name.
applications.
Dispatch can use TextExpander (iOS App
Store) (website) text snippets and also has

252
 ALTAMAIL into AltaMail and attach it from inside the
application.
Most iOS email clients focus on
fixing one or two problems with That’s not all. AltaMail also has mail rules.
email. AltaMail (iOS App I’ve talked about rules at length already in
Store) (website) is more relation to Apple Mail and Google Mail. I
ambitious. It seeks to give you a soup-to- have to admit I was a little shocked when I
nuts email client replacement with some discovered an iOS developer had the moxie
features you won’t find in Apple Mail. to add a full-blown rules system to an iOS
mail application, but that’s exactly what
A common complaint about Apple Mail is
AltaMail did. Swiping left to right on any
the backward way it goes about
email message in AltaMail gives you the
attachments.While you can attach pictures
option of creating a rule based on it. Filters
and videos to an email message from inside
exist for the the sender, recipient, copies,
Apple Mail, any other type of attachment
and subject line. Once an email satisfies the
requires you to find a separate app that
AltaMail filter, you can send it to a folder,
supports that file type and includes an
delete it, forward it, set a flag, or mark it as
option to share the file via email. AltaMail
read. Imagine opening AltaMail on your
lets you attach files from cloud storage,
iPad or iPhone and having it automatically
including iCloud, Dropbox, Google Drive,
sort and file your email for you. It is
and SugarSync, from inside AltaMail. In
possible. Another task AltaMail can perform
addition to this, you can save a file locally

253
 Creating a Mail Rule in AltaMail
Email templates are prewritten emails
AltaMail saves and lets you send over and
over again. Let’s say you are the office nerd
(like me) and your coworkers seem to have
a lot of trouble remembering the WiFi
password. You could make a template email
with instructions of how to login, the
network name, and password. Then every
time someone asks you for it (again) you
could fire up AltaMail on your iPhone and
send off the WiFi email without ever having
to type it again. Tying this feature to
AltaMail’s mail rules, you could even
automate it. If an email arrives from Lars
with the word WiFi in the subject line, send
the WiFi email template.
on a filtered message is the creation of a There are a lot of additional features in
template reply, which leads to the next AltaMail including Smart folders, multiple
interesting Alta Mail feature. account support, a unified inbox, multicolor
flags, and the ability to view the raw source

254
of an email, which is a feature I’m not aware
of on any other iOS mail application.

AltaMail seeks to provide a desktop-class

Gallery 6.8
email experience on iOS and succeeds on
several levels. Apple sets the tone for app
development on its platforms and one of
their most fundamental design principles is
that the developer sweats little details and
makes hard decisions about what features to
include. This provides a much more
streamlined computing experience that lets
the rest of us get on with our work.
AltaMail ignored this lesson and instead
provides you a big mail application that has
more features, bells, and whistles than you’d
ever expect on a mobile email client. If you The AltaMail compose window.
find yourself pining away for this experience
on your iPad and iPhone, AltaMail will 1 of 12
make your day.

255
 TRIAGE Gallery 6.9

Triage (iOS App Store) (website) is

not a new email client but instead an
email utility. The app supports Gmail,
iCloud, Yahoo, and other IMAP
accounts. (There is no Microsoft
Exchange support.)

Triage displays each email in your inbox as a card. Triage

doesn’t show you your folder structure, your archive, or
anything else. For each email card, you can flip up to
archive (or delete or mark as read), flip down to retain
and keep the message marked as unread for later, or tap
on the message to reply. If you’re out and find yourself
with five spare minutes, you could very quickly go
through your email inbox this way. Triage doesn’t solve all
of your email problems, but it does make managing your
inbox much easier. I like the simplicity of Triage.

256
 DRAFTS Gallery 6.10

In a similar vein, Drafts (iPhone Version in

iOS App Store) (iPad Version in iOS App
Store) (website) is a text authoring tool with
versions for the iPhone and iPad that can serve as an
email utility. Specifically, Draft does a great job of
capturing text. When you open Drafts, it immediately
has a cursor and is ready to go. You can then quickly
write a message using the keyboard or voice recognition
with Siri.

Drafts supports TextExpander touch (iOS App Store)

(website) so you will have the benefit of all your text
snippets at your disposal. When you’re done, you can
send the email directly from Drafts. You can even
automate this to routine correspondents. I love writing
emails in Drafts because Drafts sends email without
opening your email application.

257
 CHAPTER 7

FIGHTING SPAM
 SECTION 1

The Spam Problem

THE SPAM PROBLEM Python sketch (YouTube) involving a

restaurant where all the items on the menu
Junk mail has always been a problem. Even
included the canned meat. (As an aside, I
before we had email, junk mail was making
grew up eating SPAM often, which further
us angry. At least with the type of junk mail
explains my complete disdain for spam
that goes through the post office, merchants
email.) Geeks love Monty Python and the
have to pay for postage, which places some
word spam was frequently used in the
constraint on the amount of junk mail we
bulletin-board days of the Internet. It
receive. Imagine that instead they could mail
follows us to email and now is the common
as much junk mail through the postal system
word for all of that terrible email that tries
as they wanted without cost and you’ll get
to pull you away from the things you love.
why email is such a problem.
Experts estimate 80-85% of all email sent is
The etymology of spam is actually kind of
spam. Think about that one for a moment:
entertaining. It all started with a Monty
17 of every 20 emails sent to you are spam. I

259
guess that answers my question earlier spam. Moreover, a lot of times these emails
about what would happen if direct mail aren’t even solicitations but instead attempts
marketers didn’t have to pay postage. to get you to click something that installs the
bad guys’ robots on your
Not all spam is created equal.
computer so they can use it
Most of it is unsolicited
without you knowing in order
garbage. This is the email that
to send out even more—wait
comes from the darkest
for it—spam.
corners of the Internet trying
to sell you pornography, sexual Another type of spam,
performance drugs, and cures sometimes referred to as bacn
for male pattern baldness. This (and pronounced bacon), isn’t
spam isn’t sent to you for any as malicious as spam. This is
reason other than there is a big the email you get from online
list of email address 80-85% of email is spam. That’s a
vendors you have voluntarily
somewhere and you’re on it. If Pac-Man-sized portion of our email. done business with. I buy dress
you click on any of these shirts from the apparel
emails (even to unsubscribe), you’re telling company Lands’ End. As a result, they send
the bad guys they’ve found an email address me a lot of spammy sales emails. Lands’ End
with a human on the other side and isn’t some stranger to me or a criminal
encouraging them to send you even more enterprise but instead a legitimate vendor

260
 My Apple Mail Unsubscribe Smart Mailbox

that wants to exchange their stuff for my unsubscribe. I even have an Apple Mail
money. This type of spam is more avoidable. Smart Mailbox that looks for any email
If I unsubscribe from the Lands’ End email containing the word unsubscribe.
list, they will stop sending me solicitations.
If bacn spam is still bothering you, try a
But because I like those 30% off sales, I deal
service like Unroll.me (website). The
with their email.
service scrubs your email for you. In
Using the unsubscribe button on bacn-style addition to helping you unsubscribe, the
spam works. If you unsubscribe from service combines multiple emails into one
legitimate companies, you usually never single summary email instead of flooding
hear from them again. I am fastidious about your inbox.
this. If an unwanted email arrives from
someone I’ve done business with, I

261
 SECTION 2

Fighting Spam

SPAM SOLUTIONS between the people who send spam and the
people who block spam will never end and
The real solution to spam is to put your
as users, we do need our own solutions for
computer and email services to work for
spam that gets through the system.
you. Gmail’s antispam filters are widely
recognized as some of the best. Some people One solution to spam is mail rules. If you
use Gmail just because of their spam filters. unsubscribe to a vendor and they still send
you mail, create a mail rule to automatically
Google isn’t alone in this regard though.
delete anything they send you. Another
Apple also applies its own spam filters to
solution is to use an online service such as
iCloud mail, and any other self-respecting
SaneBox (website) to help you out.
email service provider will also look to keep
SaneBox has a feature called the
spam out of your life. The technologies they
SaneBlackHole that does a great job of
use to filter spam are actually quite
making sure you don’t see spam from the
sophisticated. But the cat-and-mouse game
same source more than once. If you’ve still

262
 got a problem with spam, spam and phishing emails. It includes
install SpamSieve on your whitelist support so you can guarantee
Mac. receiving messages from people who are
important to you. It automatically adds all of
SPAMSIEVE your previous correspondents and people in
your contacts database to the whitelist so
SpamSieve (website) is
you should never have a problem with false
the premier spam
positives. The application color codes spam
software for the Mac. This
messages so you can quickly focus on those
has been true for a long time.
that may be borderline and entirely ignore
Every few years I survey the
those that clearly are not.
field of other spam applications
on the Mac and every few years I come back One of the common tactics for spammers is
to the conclusion that this is a one-horse to embed their message in an image.
race. SpamSieve looks inside attached images and
runs its own algorithm to determine whether
SpamSieve works with most email clients on
or not it is spam. So long as you are using an
the Mac and installs a set of plug-ins that
IMAP-style mail server, once SpamSieve
does all the hard work of filtering spam for
deals with an incoming message on your
you. SpamSieve learns and adapts to your
running Mac, it will also disappear from
email so after a little use, it blocks nearly all
your mobile devices.

263
 If you’re having trouble dealing with spam
Gallery 7.1 on your Mac, go directly to SpamSieve and
install it on your Mac.

264
 CHAPTER 8

EMAIL
SECURITY
 SECTION 1

Why Email Security Matters

Take a moment to think To: Josephine some online accounts you’d

about the kinds of email you From: Napoleon prefer not to share with
have on your iPhone. There Subject: Bank Password? strangers.
is a record of every private
Once the bad guys get access
electronic conversation
I’m heading to Waterloo to your email, they’ve got
you’ve had with everyone in tomorrow and need cash but the private messages and photos.
your life. There are probably bank won’t let me login. I
They know about your favorite
confirmation emails from thought it was “shorty123” but
online retailers and often what
online services with your that’s not working. What’s the
password again? your account numbers are.
login information and even
They know where you bank
possibly passwords. You also
and who you work for. They’ve
likely have some emails to -Boni
also got access to information
your partner giving the login
about your job and, likely,
and password information for
some of your work documents.

266
They can use all of this to harvest your own
email contacts and reach out to your friends
and co-workers in attempt to hack their
email accounts using your name.

Email security should be a big deal for

everyone. This chapter is going to help you
avoid making the most common email
security mistakes and show several ways to
improve email security, including
encryption.

267
 SECTION 2

Basic Email Security

USE A REAL password system. 1Password
PASSWORD also paid for this book so what 10 Most
Common
are you waiting for? Go get it. Passwords
The security of your
email is important. In addition to creating a
Don’t use unsafe secure password for your
passwords such as your email, don’t forget to change it
birth year, ABCD, or— every once in a while.
believe it or not—password. (Did you know Whenever the clocks change in the spring
that password is the most common and fall, I change all of my major passwords
password?) I create real passwords with (including email). Email is too important for
1Password (iOS App Store) (Mac App soft passwords.
Store) (website). 1Password is on multiple
platforms and creates and stores advanced It is remarkable how much more difficult
passwords for you. The team at 1Password you can make it for hackers with a secure
works hard so you can have a responsible password.

268
Password: abc
The Cautionary Tale of
Time to Hack: 0.000004394 seconds Mat Honan’s Epic Hacking
Password: aP#ZI&#LFAIadi;#@oP Mat Honan is a well-respected writer for
Wired magazine and no stranger to
technology. In 2012, hackers broke into
Time to Hack: 45 quintillion years
Mat’s Amazon, Apple, Twitter, and
Google accounts by taking advantage of a
Did you know quintillion was a word? Neither did I. series of vulnerabilities in these
companies’ services. The hackers were
Source: HowSecureIsMyPassword.net (website) very clever.

At the time, Apple did not have two-

The 1Password New Password Generator factor authentication for its accounts and
had a policy that allowed its customer
service representatives to issue new
passwords to users over the telephone,
which could confirm a billing address and
the last four digits of their credit card.
(Not surprisingly, that is no longer the
case.)

The hackers got Mat’s billing address by

searching the records of his personal
website. To get the last four digits of his
credit card, they called Amazon, told
them they were Mat, and asked to add a
credit card to the account. At the time,
269
TWO-FACTOR AUTHENTICATION Two-factor authentication adds an
additional layer of security by requiring a
For the longest time, computer security
second validation. Most commonly this is
involved a username and a password.
done by requiring a password plus a
Usernames aren’t well protected and often
verification code delivered to the user’s
are as simple as an email address or your
mobile phone. So if the bad guys get your
name. So in order to break into your email
password, they could not get access to your
account, all the bad guys really needed was
account to change your password unless
your password. Just finding one piece of
they also had a six-digit code sent to your
data to get access to a person’s email
phone. This makes hacking your account a
account just isn’t good enough. This was
lot more difficult.
most dramatically demonstrated in the epic
hacking of Mat Honan, explained in the Both iCloud (website) and Gmail (website)
sidebar. support two-factor authentication, and I
strongly recommend enabling it. Two-factor
Service providers such as Apple and Gmail
authentication is a relatively new thing, and
realize how inherently insecure accounts are
there still are occasional problems with it. If
that only require a password. In the last few
you use the phone message method and lose
years, there have been several attempts to
your phone, you could end up getting locked
remedy this. One of the best methods is
out of your own account. On balance,
two-factor authentication.
however, I’d much rather have to jump

270
through additional hoops than make it easier
for the bad guys to hack me the way they
did Mat Honan.

271
 SECTION 3

Avoid Phishing

Email phishing is the act of sending a false then tells me I can solve all of these dreadful
email that looks as if it’s from someone the problems by just tapping a link in the email
recipient trusts and asks the recipient for and providing necessary details such as my
some personal information from which the Social Security number, the name of my
phisher can benefit. It’s shameful and the bank and account number, my mother’s
practice is not going away. As an example, I maiden name, my blood type, the vehicle
get an email nearly every day from identification number from my car, the
hypothetical PayPal (as opposed to actual location of my extra house key, and—of
PayPal). The email is always addressed to course—a list of all my Boy Scout merit
“Dear User”. It is never addressed to me badges. Phishing emails prey on people’s
personally. The email always tells me there’s good nature to believe that when the email
something critically wrong with my email says it’s from PayPal, Apple, Amazon, or
accounts, and it’s going to cost me a lot of your bank, that it actually is from that
money if I don’t fix it right away. The email company.

272
 Sample Phishing Email
The crooks behind phishing email scams get
only more sophisticated as time goes on. It
used to be that all phishing emails had a
domain listing with some foreign country
that clearly did not seem appropriate for
that company. However, the crooks have
figured out ways to spoof the emails so they
look as if they are actually coming from the
indicated company. Another telltale sign is
that the email is addressed to a generic name
such as Customer or User. If you receive an
email from your bank and it’s not directed to
your name specifically, it is a phishing email.
Rarely are phishing emails addressed to
Here is a phishing email I received while your name directly, though nowadays there
writing this chapter. Note that it is addressed are some that do.
to “User” instead of me directly and the sense
This book cannot offer you a magic solution
of urgency it conveys. “The Team” includes a
link that would lead me to a website looking a to avoiding phishing emails. There is no app,
lot like the real PayPal and asking for all of service, or plug-in that will make this go
my account information. Shameless! away. Spam filters, discussed earlier in

273
chapter 7, will help capture a lot of this type Internet through an independent search. I
of email. However, phishing emails still will know this sounds paranoid but, sadly, it is
make their way through your filters on not.
occasion. Your best defense is your wits.
Whenever someone sends you an email
asking for any kind of information, red flags
should go up and klaxons should go off in
your head.

If you have any doubt about an email, pick

up your telephone and call PayPal or Visa
or your bank. Talk to a human on the
telephone, tell them what you received, and
ask them if there is any issue with your
account. Under no circumstances should
you ever click on one of these emails until
you’ve first verified with a human that it is
for real. As an aside, when calling these
people, never use the telephone number
provided in the suspect email. Look on the
back of your credit card or look it up on the

274
 SECTION 4

Email Encryption

Even with great passwords explains how to protect and

and the best security encrypt your email.
habits, email still has its
A long time ago (well
security vulnerabilities.
maybe not that long
You are creating a
ago), people would send
message of digital words
letters to each other and
and sending it up into the
seal the envelope with a
Internet where it gets
wax seal. Delivery of a letter with the
passed around through several servers
sender’s seal intact assured the recipient
before landing in someone else’s inbox.
that the sender actually wrote and sent the
Security holes at any point of that journey,
letter and was unread in transit. Email
from the Starbuck’s WiFi to the Internet
encryption looks to bring a wax seal to your
mail servers to the recipient’s mailbox, may
Mac.
allow others to read your email. This section

275
PGP with writing email: How do your
correspondents encrypt a message to you
Pretty Good Privacy (PGP) (website) is one
without knowing your own secret
of the original commercial email encryption
encryption code so they (or anyone else) can
solutions. PGP, now owned by Symantec,
read all of your mail? PGP solves this
offers several products including PGP email
encryption. There is a unique problem faced

Screencast 8.1 The Mechanics of Public/Private Key Encryption

276
problem with public and private key both their PGP email encryption and whole-
encryption. disk encryption products. However, Apple
has since improved FileVault (which
When you set up a PGP account, you get a
handles whole-disk encryption) to such an
private encryption key, which you keep for
extent that I let my PGP subscription
yourself, and a public key, which you share
expire. For email encryption, rather than
openly. Anyone else with a PGP account
pay for a PGP license, I’m now using the
can use your public key to encrypt a
open-source alternative to PGP, GNU
message for you. Once they encrypt the
PrivacyGuard (GPG).
message, the text converts to unreadable
gibberish. Nobody can unencrypt the
message except you, using your private key.
Screencast 8.1 demonstrates how private
and public key email encryption works.

PGP is a paid service with options for

individual and larger enterprise accounts. It
can work through Apple Mail and several
other email clients. In a corporate
environment, PGP is probably the right
solution. I used to own a PGP account for

277
GPG Gallery 8.1 GPG Encryption in Apple Mail

GNU Privacy Guard (GnuPG or GPG)

(website) is an open-source mail encryption
project. It uses the same type of public/
private key encryption that PGP does.
Moreover, they’ve developed some great
tools for implementing GPG on your
platform of choice. It is very easy to set this
up for Apple Mail on the Mac using GPG
for Mail (website). This is a custom
installation of GPG that works right inside
Apple Mail. The installation process walks increasing the likelihood that you’ll be able
you through setting up your public and to locate public keys for your
private keys, and because everything works correspondents and successfully send
inside Apple Mail, adding encryption to encrypted email. Gallery 8.1 demonstrates
your email is easy. using GPG in Apple Mail.
There is a lot of momentum behind GPG Encrypted email is much more secure than
encryption in that it is free and easy to not. This, however, does come at a cost. All
install and use. As a result, there are a lot of of those services I’ve written about in this
people signing up for this encryption,

278
book that help you manage and sort email as (This works in just about every application
it arrives largely won’t work for encrypted on OS X for Mac.) Then click Save as
email. Furthermore, even though GPG has PDF… and in the next dialog box, click
greatly simplified the process of sending Security Options.... There you can insert a
encrypted email, it still adds steps and time password and save your file as an encrypted
to every email you send. I don’t recommend PDF. Then send the encrypted file to your
encrypting all email you send, but for those recipient as an email attachment. Provide
instances when encryption is more valuable your friend the password through some
than the inconvenience that comes with it,
you should at least have that option. Screencast 8.2 Encrypted PDFs on the Mac

ENCRYPTED PDF
Another way to send encrypted messages is
done via encrypted PDF attachment. This
involves the creation of your message as an
encrypted PDF file and attaching it to an
email message. You can do this anywhere in
the Mac OS using the built-in PDF tools.
To do so, click on the PDF button in the
lower-left corner of the Print dialog box.

279
means other than the enclosing email, and
they can unencrypt it on their end. The
security isn’t as complicated (or as strong)
as the PGP or GPG solutions but in a lot of
cases it is good enough. Screencast 8.2
demonstrates how to do this on the Mac.

280
 SECTION 5

The Limits of Email Privacy

Even if you follow every recommendation in program (Wikipedia). It is likely that the
this book about protecting your email, never United States isn’t the only country
forget that when it comes to email, for every conducting this sort of data collection. As
sender there is a recipient. Even if you do this book goes to press, there are even more
everything right, if your recipient keeps revelations about how sophisticated
your email message on an unlocked iPad, government snooping is. In Russia, the
the next person to sit in your friend’s airline Kremlin is so fed up with the leaky nature of
seat after she leaves it in the seat pocket can email that they’ve reverted to using
read all of your email. Because email is a typewriters (website).
communication, there are limits to what you
At some level, this is debilitating. We spend
can do about it.
so much time and effort trying to protect
In 2013, it became public knowledge that our privacy, apparently to no avail. I don’t
the United States government was capturing have answers to what we should do (or even
a lot of private email through its PRISM think) about government snooping, but I

281
still believe strongly in email security. Even
if your correspondents are sloppy and the
guys in black hats are reading our email,
good email security habits can keep a lot of
other people out.

Finally, accept that these communications

aren’t entirely secure and think about what
you write in an email. If you’re not
comfortable with the contents of your email
on the front page of your local newspaper,
think really hard before sending it in an
email.

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 CHAPTER 9

ARCHIVE
 SECTION 1

Apple Mail Export

Whether you are using a native mail client down from the cloud. There are several
such as Apple Mail or a web-based solution tools to pull this off.
such as Gmail, there
One of the easiest ways
may be performance or Screencast 9.1 Exporting Mailboxes in Apple Mail
to make an extra copy
privacy reasons for you
of your email files from
to save portions of
Apple Mail is the
your email to an
Mailbox→Export
archive. Apple Mail
will slow down with Mailbox... Menu bar
large libraries and selection. You can
while Gmail is great, export a mailbox to an
there is something to external drive and have
be said for pulling a your very own backup.
copy of your emails There is no way to
analyze or search the
284
emails in that database short of importing it
back into Apple Mail, but if you are looking
for a quick and dirty way to make a copy of
your Apple Mail folders, there is none
quicker or dirtier.

285
 SECTION 2

MailSteward

For a long time, MailSteward Speaking of performance, MailSteward has

(website) has been the go-to the same challenges as Apple Mail when the
solution for email archives on database gets too big. It can slow down the
your Mac. MailSteward will more demands you place on it. In my
copy your entire Apple Mail experience, when a database starts
email database (including attachments) to approaching 100,000 messages, you’ll need
its own separate database. You can search to make a new database. MailSteward Pro
the MailSteward database at will to find will save to a more robust MySQL database
your old messages when you need them that will give you more breathing room.
later. Moreover, because you’ve placed all of However, I doubt this will be necessary for
your email in a separate searchable many individual users.
database, you can delete large portions of
There are several settings in MailSteward so
your existing email database, improving
you can tell it what to backup and when to
performance.
do it. You can select specific mailboxes,

286
accounts, and time Gallery 9.1 from a coworker
periods. gets a Work tag.
MailSteward can That can make
also automatically future searches
delete emails as it much easier.
archives them from
I’ve owned
your database. Be
MailSteward for
warned, however,
years, but I’ve
MailSteward is not
never been able to
designed to put
bring myself to
messages back into
actually delete
your email library.
messages from my
MailSteward has email database after
several useful archiving them. I’ve
features including never felt as if my
scheduling, which will automate the archival Mac couldn’t keep up with my email
process, and tags. MailSteward will use database (which is now at 115,000
rules to add tags for the MailSteward messages). I suspect this is a combination of
database upon export from Apple Mail. For software improvements Apple has made
instance, I could add a tag that any emails with OS X for Mac and Apple Mail and my

287
obsession with getting a new Mac every two
or three years, but I’ve never had the kind
of performance problems that required me
to delete old emails. Nevertheless, having an
external copy of my email database seems
like a good idea, and MailSteward does this
job reliably. Gallery 9.1 includes several
Mail Steward screenshots.

288
 SECTION 3

Email Archiver

Email Archiver (Mac App Store) attachments, Email Archiver will

(website) is a more recent create a separate folder with
arrival in this space. Created the email name holding all the
by Ironic Software (website), attachments.
Email Archiver takes a
Because it is a PDF export, this
different approach.
app is also useful for archiving just the
Instead of rebuilding your
emails from a project. Gallery 9.2 includes
email in a searchable database,
some screenshots but there really isn’t much
Email Archiver exports all of your
to this application. You run the archive and
email as PDF files in hierarchical folders.
then navigate the nested folders to your
These folders are organized by date with the
desired folder.
same structure as your email database, and
Spotlight on your Mac will search the entire I really like the idea of an email archive not
database for you. If there are message tied up in a database but instead a list of

289
PDF files. I wrote about this a lot more in
Paperless (iBooks Store) (website), but the
less we rely on some proprietary format for
our data, the better. Indeed, I like Email
Archiver so much that it has replaced
MailSteward for my email archiving Gallery 9.2
needs.

Email Archiver has one of the simplest user

interface buttons I’ve ever seen.

290
 SECTION 4

Archiving Gmail

Archiving web-based email is a good idea. purpose of making an

Companies such as Google understand archive. If you do that,
backup, and I can’t imagine them losing all any of the options
of your online email, but why leave this up already covered in this
to them? chapter would work.

Google has faced this issue head-on with the If you are heavily invested in
Google Takeout service, that lets you the Google lifestyle, try using CloudPull
download your Google email and data. (website). CloudPull pulls down all of your
Google data for a local backup. It is really
Another option is to use a local client. Even
good at copying your Gmail, including the
if you prefer using Gmail through the
ability to pull messages or Gmail labels into
website (like I do), you can still occasionally
Apple Mail as mailboxes. It also imports
fire up a local client, such as Apple Mail,
your Google contacts, calendars, and
and connect it to your Gmail account for the
documents from Google Drive. Out of the

291
box, CloudPull a Gmail or Yahoo mail account. These aren’t
backs up your active accounts but simply an online
Google data every destination for copies of important emails
hour and is an they’d like to keep. I get the convenience of
excellent solution if you’ve got a lot of data this, but I prefer email archives on hard
on Google servers. drives that I own and control. I’d
recommend the other approaches covered in
Another option for backing up Gmail is
this chapter.
Backupify. (website)

Backupify can back up Gmail (and other

Google data. You can do a backup of your
gmail to your local computer. The service
also includes an option to password
protect .zip files of your email.including the
ability to password protected .zip files.

BACKING UP TO AN ONLINE
ACCOUNT
Another method some people use for backup
is sending a blind copy of all their emails to

292
 SECTION 5

Saving Individual Emails

Archiving all of your emails is great, but

sometimes you just need to save a single Screencast 9.2 Printing an Email to PDF

email to PDF. That is painless on the Mac.

With Mavericks, Apple added a new
keyboard shortcut to Apple Mail,
Control+Option+Command+P, that saves
the email to PDF. (It also will work with
multiple selected emails.) Gmail also has a
mechanism for saving an email to PDF. If
you want help figuring out what to do with
those email PDFs after export, read my
Paperless Field Guide (iBooks Store).

293
 CHAPTER 10

EMAIL
WORKFLOWS
At this point in the book, you are already an that makes you nuts, go here in your
email ninja. You’ve also figured out that browser (website) and you can download all
there is not any one be-all and end-all the audio files for import into iTunes.
solution for email. This chapter pulls it all
together where I share my own personal
email workflow.

I also conduct audio interviews of some of

my brilliant friends about how they deal
with email. I chose people from many walks
of life for these interviews. There are
doctors, educators, IT specialists, writers,
directors, actors, and producers. They all
have large email demands placed on their
time, and a lot of them use different email
systems and technologies to cope. They are
all wicked smart.

There is a technical limitation with iBooks

that will stop playing the audio file in these
interviews when you change the page. If

295
 SECTION 1

My Email Workflow

MY EMAIL ACCOUNTS that I share with friends and family and

manage my personal correspondence.
I'm a man of many mailboxes.
My law firm uses Microsoft Office 365
There are several aspects of my life
including their hosted Exchange. As
that I would like to think stand
such, everyone in the firm has Microsoft
independent of one another. I'm a
Exchange email, calendar, contacts
dad. I'm a geek. I'm a lawyer. For my
database and all the other Exchange-y
personal email, I use an iCloud account.
bits that come with it.
Years ago I had this on a local Internet
Service Provider email account but moved it On the geek side, I have multiple email
to an Apple @mac.com account. Then Apple addresses. I have an email address related
transitioned @mac.com to MobileMe and to the Mac Power Users podcast, several
now, most recently, they've transitioned to related to MacSparky, including feedback
iCloud. Regardless, this is the email account and other pieces relating to the publishing

296
 My Email Accounts

business. I've set up all of those accounts to traditional IMAP account (although I spent
point to the david@macsparky.com account. some time with that account as a Gmail
If you send me an email from any of my tech account, explained
related goings-on, it is going to get later). My personal
automatically forwarded into that account. email is through
At the end of the day, I'm managing three iCloud.
important email accounts in my life.
My primary email
Each of these three accounts use different application is Apple
technologies. The day job account uses Mail for both the Mac
Microsoft Exchange. MacSparky uses a and iOS. While a lot of

297
geeks, myself included, have poked fun at every day but instead I primarily use it
Apple Mail over the years, the fact is Apple when I get busy, know my inbox is filling
has improved this product a great deal and up, and I don't have time to deal with it in
added features that I find extremely useful, full detail. Because I use SaneBox, my inbox
such as VIPs, better keyboard support, an is already filtered and a lot of emails aren’t
outstanding set of mail rules, Smart in Dispatch for processing.
Mailboxes, and several of the other features
I covered in this book. FLIRTING WITH
On occasion, I've been GMAIL
known to use third-party In the process of
applications, particularly writing this book, I
on iOS. I like the way iOS spent a lot of time
mail tools have cropped up using applications
to solve little email problems without trying that I covered in
to replace Apple Mail entirely. One of the chapter 6 (and quite a few more applications
best I've encountered for this purpose is that didn't make the cut). I was most
Dispatch. It lets me quickly filter through interested in Gmail.
the emails in my personal and MacSparky
accounts and reply or set them aside for I started this journey inclined to switch to
further processing. I don't use Dispatch Gmail permanently. A lot of friends that I

298
know and respect use Gmail all the time and powerful, even though they didn't reside on
prefer it for managing their email. Gmail's the Internet. (I leave Apple Mail running on
inbox categories, label system, amazing our family iMac so my mail rules are always
search, and keyboard shortcuts is a pretty working for me.)
tempting concoction of technology.
Additionally, I still had an iCloud account
So I used it exclusively for a while, but for personal mail and my Microsoft
ultimately (and surprisingly) I returned to Exchange account for the day job. While
IMAP and Apple Mail as my primary email those accounts worked fine in Apple Mail,
technology in the end. Using Gmail day-to- Gmail did not. If I was going to use Gmail, I
day, I found that I didn't use labels as much wanted to get the advantage of all the Gmail
as I thought I would. I had the same technologies, which required me to use it in
experience a few years ago with MailTags the web or a Gmail-specific application. So I
on the Mac. I am just resistant to taking the routinely found that I was going to two
time to tag emails because search is so good different places to manage my email. It was
that I rarely find I miss them. this tedium that ultimately broke my will of
staying with Gmail. If I had just one email
During my Gmail phase, I found that there
account, Gmail would have been more
were some features I missed from Apple
compelling.
Mail, such as VIPs, Automator services, and
my Apple mail rules which were more

299
Interestingly, despite all my blathering Having made this world tour of mail
about privacy in the way that Gmail serves applications, I surprised even myself to
ads, once I started using Gmail, that didn't discover that the best solution for me
bother me. Perhaps it's the PRISM remains Apple Mail. In addition to the
disclosures that seem to come out every day, features covered in this book, it also
but I just don't assume much email is private integrates with the operating system like
anymore. only an application developed by Apple can.
It's also scriptable and, overall, gives me a
Another reason why I ultimately gave up on
tremendous amount of options and ways for
Gmail was the power of SaneBox. My
dealing with my email.
SaneBox account provides me a lot of the
features (particularly inbox filtering) that I
liked about Gmail. Indeed, in my MANAGING EMAIL VOLUME
experience, SaneBox does a better job of it The big problem I face is the volume of
and adds additional features such as email I receive. I'm fortunate to have a lot of
deferred email and reminders. In summary, people writing me. I love hearing from
while I enjoyed my fling with Gmail, I'm people that read my books or listen to my
perfectly happy with my IMAP accounts podcasts and want to share something with
moving forward. me. I love even more when people write me
and tell me how something I've done has
made their life a little bit better. It is those

300
emails that inspire me to keep giving more And finally I receive a lot of email on my
and working harder. personal account from friends, family,
vendors I've dealt with, and all the other
I also get a lot of emails from people asking
bits of email that everyone is all too familiar
me questions about advice over what to buy,
with.
what to use, or how to pull off a particular
vexing problem. Some of these emails are So I've got all of these buckets of email
easy to respond to, and some of them take coming at me that add up to a large volume
quite a bit more time. In addition, a lot of of incoming correspondence. In fact, it's just
people send me emails talking about too much for me to manage with the Inbox
products they are creating or software they Zero approach of clearing out the inbox and
are writing and asking for my opinion about managing it all with just a few folders.
what they are up to. All of these emails are Instead, I use additional inboxes on
extraordinarily flattering. each account to perform
a rough filtering of
Then I get email related to my day job.
my emails, which
Clients have questions. Opposing counsel
gives me different
will write me concerning the latest bit of
places with relative
litigation, and I receive emails relating to my
priorities for email
commitments and professional
review and processing.
organizations.

301
Largely, I pull off this trick with me, largely automatically. (I am
SaneBox. I cannot overstate how The MacSparky Account still amazed at how reliable
Mailbox List
much I love using this service. It is SaneBox is at this seemingly
particularly useful in helping me subjective decision.) I also have
manage the MacSparky account, a SaneBox folder on the
where I get the largest volume of MacSparky account called
email. I have SaneBox watching my "Later".
MacSparky inbox. Over time,
I have a SaneBox News
SaneBox has learned where I want
mailbox on this account where I
my email sorted. If I get an email
send emails concerning press
from Apple or someone I'm working
releases, new products, and
with at Macworld or on one of the
other news-type items related to
books, it leaves it in the inbox.
my MacSparky life.
I have another SaneBox mailbox
Email that SaneBox doesn't
called "Feedback". Whenever I
think important enough to leave
receive a question or comment from
in the inbox but also doesn't
a reader or listener, I always move it
think logically fits in Feedback
from the inbox into that Feedback
or News folder goes in the
folder. Over time, SaneBox has
SaneBox Later mailbox. So as I
figured this out and now does it for

302
 Mailbox Review Frequency

wake up in the morning, I'll have a few I clear out the Later mailbox once a day.
items in my inbox, and several more items Sometimes clearing out this inbox means
already sorted in the Later, News, and simply giving SaneBox more data. For
Feedback mailboxes. example, there may be feedback-style emails
in there that I move to the Feedback
I try to tackle each of those mailboxes with
mailbox or news-related items that get
their relative level of importance. The inbox
moved to the News mailbox. I do this using
always gets managed with an Inbox Zero
keyboard shortcuts in Apple Mail (the
methodology several times a day. I clear it at
Control+Command+Number trick covered
least every morning and afternoon.
in chapter 4) if I'm doing this on my Mac.
Sometimes I'll hit it more often depending
Other mail in the Later mailbox that doesn't
on what I'm doing.

303
fit somewhere else gets handled right then (when Sarah isn't playing with LEGO
using the Inbox Zero method. bricks) specifically for that purpose.
Moreover, I don't feel stressed about those
I haven't yet mentioned my Action folder
emails during the rest of the week because I
because it is not a SaneBox mailbox, but it
know they're put in a separate place and
does exist and I'll frequently send items
that I will have time to go through them
from the inbox or Later mailbox to the
later. It takes an hour or two to get through
Action folder. The Action folder always gets
it all, but when I'm done I always feel good
managed at least once every couple of days.
about myself not only because I managed to
This is a lot easier because a large volume of
keep up with the feedback email but also
email has gone into the feedback and news
because the people who write me are
mailboxes.
generally really nice and make me feel great.
Once a week I sit down and go through the Another improvement in my mental
Feedback folder. Segregating it in this way workflow is the ability to file some emails
makes going through the feedback so much without reply. Not everything needs a reply.
more enjoyable. The vast majority of email The News Mailbox gets reviewed less often.
in that Feedback folder is people just like If things get really busy, I may dump a
me and have interesting questions and bunch of the news folder without even
comments. I don't feel stressed about those reading it.
emails because I'm doing them at a set time

304
When I first started writing this book, I was deferring email since I'm using it all the
pretty hostile to the idea of deferred email. time.
Several email apps in this book, including
I could pull this all off manually without
MailPilot and SaneBox, offer specialized
SaneBox. I could go through my inbox and
mailboxes that hold email in limbo for a day,
sort items manually into Feedback, News,
a week, or some other set period to get it off
Later, and Action folders. However, I much
your plate in the interim.
prefer paying SaneBox to do this for me.
In the process of testing this idea for the Waking up to five items in my inbox instead
book, it has grown on me. Now I use three of 70 makes SaneBox absolutely worth it to
such mailboxes through my SaneBox me.
account: one day, one week, Saturday. Some
I don’t sort sent email. My MacSparky.com
email gets put into these boxes. I find I use
account has a large “sent” mailbox than I
them when I have a non-critical email that
can search the same way I search my
will still take some work before responding,
archive mailbox. For people that instead use
and I don't want the emotional weight of
project related mailboxes or tags, it would
seeing it. For me it has become an
make more sense to tag or save the related
intermediary step between the Action folder
sent emails there.
and creating a specific task in OmniFocus to
managing the email at some date in the I use a similar workflow with my personal
future. I can no longer be critical of email. I have SaneBox automatically sort

305
Later and News mailboxes. The volume isn’t different buckets of correspondence that I
nearly as high on my personal account but deal with in their relative levels of priority. I
separating the news helps a lot. Like the use all of the Apple Mail tools covered in
MacSparky account, I clear my inbox every this book to get my Mac and iOS devices
day and my Action folder every few days managing as much of this as possible
and my News folder whenever I get around without requiring my direct involvement. I
to it. manage to deal with the truly urgent email
on a timely basis and do a pretty good job of
For my day-job account, I don't use
dealing with the rest without turning my life
SaneBox. I manually manage my inbox on
upside down every day. Despite the large
that account with the Inbox Zero method.
volume of email I receive, I finally feel like
SaneBox gets quite a bit more expensive
I'm not drowning in it, and that feels pretty
when you add a third SaneBox email
good.
address and I'm still not sure I want
anything related to client email going
through any other servers. Moreover, the
volume is low enough that it is entirely
manageable.

Pulling all of these technologies together,

I've found my peace with email. I have

306
 SECTION 2

Serenity Caldwell: Writer

Serenity Caldwell (website) (Twitter) writes Audio 10.1 Serenity Caldwell Audio
about technology for Macworld magazine Interview

(website). She also rocks the roller derby

circuit for the Boston Derby Dames
(website). Serenity deals with a lot of email
and has some great tips.
307
 SECTION 3

Rob Corddry: Producer and Actor

Rob Corddry is best known

as an actor and producer
(IMDb) (Twitter). Rob
uses Apple technologies to
manage an extremely busy
schedule and shares his
thoughts on email with me.

Audio 10.2 Rob Corddry Audio

Interview

308
 SECTION 4

Merlin Mann: Writer and Broadcaster

Merlin Mann (website)

(Twitter) is, in my mind at least,
the original productivity
blogger. One of the things I love
about Merlin is that while he
enjoys the nerdy, fiddly parts,
he also likes talking about the
big picture and underlying Audio 10.3 Merlin Mann Audio
problems we face with email. Interview

309
 SECTION 5

Fraser Speirs: Educator

Fraser Speirs (webpage)(Twitter) is one of

the foremost authorities on using the iPad in
education. Fraser is a teacher and geek. He Audio 10.4 Fraser Speirs Audio
Interview
spends a lot of time traveling and sharing his
experiences with other educators and has, as
a result, an ever-growing inbox. Fraser
shares his email workflow.

310
 SECTION 6

Jeff Taekman: Physician

Jeff Taekman (website)

(Twitter) is an anesthesiologist
and academic physician at
Duke University. As a doctor
and educator, Jeff receives a lot
of email and has some great
ideas on how to cope. Audio 10.5 Jeff Taekman Audio
Interview

311
 SECTION 7

Aisha Tyler: Entertainer

Aisha Tyler (IMDb)(website)

(Twitter) is a well known
actress, comedian, writer and
emerging director. Aisha is
very popular and receives a
great deal of email. Aisha was
kind enough to share the tools
she uses to handle her email
while still having time to Audio 10.6 Aisha Tyler
create things. Audio Interview

312
 SECTION 8

David Wain: Director and Writer

David Wain (IMDb) (website)

(Twitter) is a really talented
guy. He comes up with ideas,
writes a script, directs the
movie, and then does the post-
production. Usually, David has
several of these projects going
on at once. David is also a
Audio 10.7 David Wain
Gmail power user. In this Audio Interview

interview, David shares some

great email tips and explains
how he uses Gmail.

313
 SECTION 9

Gabe Weatherhead: IT Specialist

Gabe Weatherhead (website)

(Twitter) is a trained scientist
turned IT manager. Gabe is
responsible for a large
computer network and can’t
afford to miss an email. Gabe
has spent a lot of time thinking
Audio 10.8 Gabe Weatherhead
about email and shares some of Audio Interview
his wisdom in this interview.

314
APPENDIX
 SECTION 1

Lick a Stamp

Now that I’ve shared over 1.1GB worth of

data with you about how to get better at
email, I’d like to share my deep, dark secret.
Once in a while, I like to lick a stamp and
send a note the old-fashioned way. There
are occasions where an email is not the
appropriate medium. When a friend has a
new baby, gets that promotion, graduates, or
loses a loved one, it makes more sense to 1. GET SOME QUALITY STATIONERY
send someone a handwritten note. Of Sending a note on a piece of plain white
course, I have a workflow for that too. copy paper is not going to cut it. I’m also not
a fan of buying a preprinted greeting card.
You are doing something special. Don’t use
ordinary materials. Instead, go to a

316
stationery store and buy If you’d like, you could
yourself a nice box set of write these notes on the
stationery and matching computer and then use a
envelopes. I used store- nice script font to print
bought paper for years, them, but I just print
but recently I’ve started them nicely. I think there
having my own stationery is something special about
printed by Hoban Press using your pen instead of
(website). I’m a big fan of a printer, even with
Hoban Press and would recommend it, but dreadful script. Think about the text inside
if that doesn’t work, there are a lot of online your note before you start writing. Nice
stores that sell customized stationery. stationery is expensive, and you don’t want
to waste it. I’ve even been known to write
2. WRITE YOUR NOTE handwritten or iPad-based drafts before
putting pen to paper.
This is perhaps the hardest part for me, not
because I have trouble composing the words
but because my handwriting is so terrible. I 3. GO MEDIEVAL ON YOUR
gave up on handwriting in sixth grade and, ENVELOPE
thus, have the handwriting of a fifth-grader. You aren’t going to be sending these
handwritten notes very often so why not

317
make it truly special? Get yourself a wax
seal. You can get them online from
numerous vendors.

I have one with a big S on it and several

sticks of sealing wax. Heat your wax over a
candle (or match) and drip the wax on the Gallery 11.1 Dumping Email for Something More Traditional

backside of your envelope so that the wax

drips on the seam between the envelope lid
and paper. Once you’ve got a nice puddle of
wax, but before it starts to cool and harden,
press your seal into the wax like Richard
III, and hold it there for a minute while the
wax cools. Lift your seal and you’ve got a
note that’s going to make somebody’s day.

As a last touch, I was in the post office and

saw they were selling commemorative Miles
Davis Stamps. I bought $40 worth and now
even my postage reflects me.

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 SECTION 2

More MacSparky Resources

MacSparky.com Mac Power Users Podcast

Website iTunes
Twitter Website
5by5
Episode 164 on Email
Episode 224 on Email

319
 SECTION 3

Contact and Feedback

FEEDBACK anyone and not pester you unless I have

something really interesting.
Every MacSparky Field Guide gets free
updates for at least two years following Newsletter Sign Up
publication. Have a suggested change? Send
me an email.
IBOOKS STORE REVIEW?
David@MacSparky.com Did you enjoy this book? If you did, I’d
really appreciate an iBooks Store review.
NEWSLETTER Reviews help me find new readers and that
helps me write more MacSparky Field
Want to keep up with the MacSparky Field
Guides. Pretty please?
Guides? Sign up for the newsletter. I
promise I will never share your email with
320
 SECTION 4

Credits

EDITOR AUDIO EDITOR

Leilani Resurreccion “If you ever find you need help J.F. Brissette
Twitter
again, you know, if you’re in
COVER DESIGN trouble, need a hand out of a
Darren Rolfe BETA TEAM
corner ...”
Twitter J.F. Brissette
“Yeah?”
The Mighty Monocle
Jean MacDonald
“Please don’t hesitate to get
Twitter
ILLUSTRATIONS lost.” Website
Mike Rohde –Douglas Adams, The Restaurant
Eddie Smith
Twitter at the End of the Universe Twitter
Website
Website

321
IMAGE CREDITS Archive Boxes - ©depositphotos/toxawww

Chapter 1 Chapter 10
Stack of mail - ©depositphotos/windujedi Woodworking - ©depositphotos/zigzagmtart

Lego Mac - ©david sparks. I purchased that kit from Chris Microphone - ©depositphotos/alexroz
McVeigh (website).
Microphone on Audio Interviews - ©depositphotos/
Chapter 2 Dragan Jovic

Compass on Map - ©depositphotos/miflippo Appendix

Chapter 3 Stack of Books - ©depositphotos/nanka-photo

Gears - ©depositphotos/korovin

Chapter 4
MacBook Keyboard - ©depositphotos/CreativeNature

Chapter 8
Vault Door - ©depositphotos/paulfleet

Lock and Key - ©depositphotos/fotoall

Chapter 9

322
 SECTION 5

Legal Mumbo Jumbo

Email, A MacSparky Field Guide, Ver. 1.2 Bulgaria, Canada, Chile, Colombia, Costa
Rica, Cyprus, Czech Republic, Denmark,
Lawyers ruin all the fun.
Dominican Republic, Ecuador, El Salvador,
Copyright © 2013, 2014 David Sparks Estonia, Finland, France, Germany, Greece,
Guatemala, Honduras, Hungary, Ireland,
Published by David Sparks Italy, Latvia, Lithuania, Luxembourg,
Foothill Ranch, California Malta, Mexico, Netherlands, New Zealand,
Nicaragua, Norway, Panama, Paraguay,
Lovingly hand-crafted in the United States Peru, Poland, Portugal, Romania, Slovakia,
of America. Slovenia, Spain, Sweden, Switzerland,
United Kingdom, the United States of
ISBN: 978-0-9854561-3-9
America, and Venuzuela.
Published simultaneously in Argentina,
Australia, Austria, Belgium, Bolivia, Brazil,

323
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Publisher. Requests to the Publisher for
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and related trade dress are trademarks of
David Sparks, and may not be used without
written permission.

324
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Warranty therefrom. You are big boys and girls and
need to make your own decisions. The fact
Of course the lawyer had to add this. The
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325