Cryptography and

Network Security
Edition
by William Stallings
 Chapter 2
Classical Encryption
Techniques
"I am fairly familiar with all the forms of secret
writings, and am myself the author of a trifling
monograph upon the subject, in which I analyze
one hundred and sixty separate ciphers," said
Holmes.

—The Adventure of the Dancing Men,

Sir Arthur Conan Doyle
 Symmetric Encryption
• Also referred to as conventional encryption or single-key
encryption

• Was the only type of encryption in use prior to the

development of public-key encryption in the 1970s

• Remains by far the most widely used of the two types of

encryption
 Basic Terminology
• Plaintext
• The original message • Cryptographic system or
cipher
• Ciphertext • Schemes used for
encryption
• The coded message
• Cryptanalysis
• Enciphering or encryption
• Techniques used for
• Process of converting from deciphering a message
plaintext to ciphertext without any knowledge of
the enciphering details
• Deciphering or decryption
• Restoring the plaintext • Cryptology
from the ciphertext • Areas of cryptography and
cryptanalysis together
• Cryptography
• Study of encryption
 Simplified Model of
Symmetric Encryption
Model of Symmetric
Cryptosystem
 Cryptographic Systems
• Characterized along three independent dimensions:

The type of operations

The number of keys The way in which the
used for transforming
used plaintext is processed
plaintext to ciphertext

Symmetric,
single-key, secret-
Substitution Block cipher
key, conventional
encryption

Asymmetric, two-
Transposition key, or public-key Stream cipher
encryption
 Cryptanalysis and
Brute-Force Attack

Cryptanalysis Brute-force attack

• Attack relies on the nature of the • Attacker tries every possible key on
algorithm plus some knowledge of the a piece of ciphertext until an
general characteristics of the plaintext intelligible translation into plaintext
• Attack exploits the characteristics of is obtained
the algorithm to attempt to deduce a • On average, half of all possible keys
specific plaintext or to deduce the key must be tried to achieve success
being used
Encryption Scheme Security
• Unconditionally secure
• No matter how much time an opponent has, it
is impossible for him or her to decrypt the
ciphertext simply because the required
information is not there

• Computationally secure
• The cost of breaking the cipher exceeds the
value of the encrypted information
• The time required to break the cipher
exceeds the useful lifetime of the
information
 Brute-Force Attack

Involves trying every possible key until an intelligible

translation of the ciphertext into plaintext is obtained

On average, half of all possible keys must be tried to

achieve success

To supplement the brute-force approach, some

degree of knowledge about the expected plaintext
is needed, and some means of automatically
distinguishing plaintext from garble is also needed
 Substitution Technique
• Is one in which the letters of plaintext are
replaced by other letters or by numbers or
symbols

• If the plaintext is viewed as a sequence of bits,

then substitution involves replacing plaintext
bit patterns with ciphertext bit patterns
 Caesar Cipher
• Simplest and earliest known use of a substitution
cipher
• Used by Julius Caesar
• Involves replacing each letter of the alphabet with
the letter standing three places further down the
alphabet
• Alphabet is wrapped around so that the letter
following Z is A
plain: meet me after the toga party
cipher: PHHW PH DIWHU WKH WRJD SDUWB
 Caesar Cipher Algorithm
• Can define transformation as:
a b c d e f g h i j k l m n o p q r s t u v w x y z
D E F G H I J K L M N O P Q R S T U V W X Y Z A B C

• Mathematically give each letter a number

a b c d e f g h i j k l m n o p q r s t u v w x y z
0 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25

• Algorithm can be expressed as:

c = E(3, p) = (p + 3) mod (26)

• A shift may be of any amount, so that the general Caesar algorithm is:

C = E(k , p ) = (p + k ) mod 26

• Where k takes on a value in the range 1 to 25; the decryption algorithm is

simply:

p = D(k , C ) = (C - k ) mod 26
 Brute-Force
Cryptanalysis of
Caesar Cipher

(This chart can be found on

page 35 in the textbook)
Sample of Compressed Text
 Monoalphabetic Cipher
• Permutation
• Of a finite set of elements S is an ordered sequence of all
the elements of S , with each element appearing exactly
once

• If the “cipher” line can be any permutation of the

26 alphabetic characters, then there are 26! or
greater than 4 x 1026 possible keys
• This is 10 orders of magnitude greater than the key space
for DES
• Approach is referred to as a monoalphabetic substitution
cipher because a single cipher alphabet is used per
message
 Monoalphabetic Ciphers
• Easy to break because they reflect the frequency
data of the original alphabet
• Countermeasure is to provide multiple substitutes
(homophones) for a single letter
• Digram
• Two-letter combination
• Most common is th

• Trigram
• Three-letter combination
• Most frequent is the
 Playfair Cipher
• Best-known multiple-letter encryption cipher
• Treats digrams in the plaintext as single units and
translates these units into ciphertext digrams
• Based on the use of a 5 x 5 matrix of letters
constructed using a keyword
• Invented by British scientist Sir Charles
Wheatstone in 1854
• Used as the standard field system by the British
Army in World War I and the U.S. Army and other
Allied forces during World War II
 Playfair Key Matrix
Fill in letters of keyword (minus duplicates) from
left to right and from top to bottom, then fill in
the remainder of the matrix with the remaining
letters in alphabetic order
We must now split the plaintext up into digraphs (that is pairs of letters). On
• Using the keyword MONARCHY: each digraph we perform the following encryption steps:
• If the digraph consists of the same letter twice (or there is only one letter
left by itself at the end of the plaintext) then insert the letter "X" between
M O N A R the same letters (or at the end), and then continue with the rest of the
steps.
C H Y B D • If the two letters appear on the same row in the square, then replace each
letter by the letter immediately to the right of it in the square (cycling round
E F G I/J K to the left hand side if necessary).
• If the two letters appear in the same column in the square, then replace
L P Q S T each letter by the letter immediately below it in the square (cycling round to
U V W X Z the top of the square if necessary).
• Otherwise, form the rectangle for which the two plaintext letters are two
opposit corners. Then replace each plaintext letter with the letter that forms
the other corner of the rectangle that lies on the same row as that plaintext
letter (being careful to maintain the order)
 Hill Cipher
• Developed by the mathematician Lester Hill in
1929
• Strength is that it completely hides single-
letter frequencies
• The use of a larger matrix hides more frequency
information
• A 3 x 3 Hill cipher hides not only single-letter but
also two-letter frequency information

• Strong against a ciphertext-only attack but

easily broken with a known plaintext attack
 Hill Cipher (Cont.)
The Hill Cipher uses an area of mathematics called Linear Algebra, and in particular requires
the user to have an elementary understanding of matrices. It also make use of Modulo
Arithmetic (like the Affine Cipher). Because of this, the cipher has a significantly more
mathematical nature than some of the others. However, it is this nature that allows it to act
(relatively) easily on larger blocks of letters.

In the examples given, we shall walk through all the steps to use this cipher to act on digraphs
and trigraphs. It can be extended further, but this then requires a much deeper knowledge of
the background mathematics. Some important concepts are used throughout: Matrix
Multiplication; Modular Inverses; Determinants of Matrices; Matrix Adjugates (for finding
inverses).

More visit: http://crypto.interactive-maths.com/

 Hill Cipher (Cont.)
Encryption
To encrypt a message using the Hill Cipher we must first turn our keyword into a key
matrix (a 2 x 2 matrix for working with digraphs, a 3 x 3 matrix for working with
trigraphs, etc). We also turn the plaintext into digraphs (or trigraphs) and each of
these into a column vector. We then perform matrix multiplication modulo the length of
the alphabet (i.e. 26) on each vector. These vectors are then converted back into
letters to produce the cipher text.
With the keyword in a matrix, we need to convert this into a key matrix. We do this by converting each letter
into a number by its position in the alphabet (starting at 0). So, A = 0, B = 1, C= 2, D = 3, etc
To perform matrix multiplication we "combine" the top row of the key matrix with the column vector to get the top
element of the resulting column vector. We then "combine" the bottom row of the key matrix with the column vector
to get the bottom element of the resulting column vector. The way we "combine" the four numbers to get a single
number is that we multiply the first element of the key matrix row by the top element of the column vector, and
multiply the second element of the key matrix row by the bottom element of the column vector. We then add
together these two answers

Decryption
(Homework???)
 Polyalphabetic Ciphers
• Polyalphabetic substitution cipher
• Improves on the simple monoalphabetic
technique by using different monoalphabetic
substitutions as one proceeds through the
plaintext message

All these techniques have the following

features in common:
• A set of related monoalphabetic substitution
rules is used
• A key determines which particular rule is
chosen for a given transformation
 Vigenère Cipher
• Best known and one of the simplest
polyalphabetic substitution ciphers

• In this scheme the set of related

monoalphabetic substitution rules
consists of the 26 Caesar ciphers with
shifts of 0 through 25

• Each cipher is denoted by a key letter

which is the ciphertext letter that
substitutes for the plaintext letter a
 Example of Vigenère Cipher
• To encrypt a message, a key is needed that
is as long as the message
• Usually, the key is a repeating keyword
• For example, if the keyword is deceptive,
the message “we are discovered save
yourself” is encrypted as:
key: deceptivedeceptivedeceptive
plaintext: wearediscoveredsaveyourself
ciphertext: ZICVTWQNGRZGVTWAVZHCQYGLMGJ
Decryption
(Homework???)
Vigenère Autokey System
• A keyword is concatenated with the plaintext
itself to provide a running key
• Example:
key: deceptivewearediscoveredsav
plaintext: wearediscoveredsaveyourself
ciphertext: ZICVTWQNGKZEIIGASXSTSLVVWLA
• Even this scheme is vulnerable to cryptanalysis
• Because the key and the plaintext share the same
frequency distribution of letters, a statistical
technique can be applied
Vernam Cipher
 One-Time Pad
• Improvement to Vernam cipher proposed by an Army Signal Corp
officer, Joseph Mauborgne

• Use a random key that is as long as the message so that the key
need not be repeated

• Key is used to encrypt and decrypt a single message and then is

discarded

• Each new message requires a new key of the same length as the
new message

• Scheme is unbreakable
• Produces random output that bears no statistical relationship to the
plaintext
• Because the ciphertext contains no information whatsoever about
the plaintext, there is simply no way to break the code
 Difficulties
• The one-time pad offers complete security but, in practice,
has two fundamental difficulties:
• There is the practical problem of making large quantities of
random keys
• Any heavily used system might require millions of random
characters on a regular basis
• Mammoth key distribution problem
• For every message to be sent, a key of equal length is needed
by both sender and receiver

• Because of these difficulties, the one-time pad is of limited

utility
• Useful primarily for low-bandwidth channels requiring very
high security

• The one-time pad is the only cryptosystem that exhibits

perfect secrecy (see Appendix F)
 Rail Fence Cipher
• Simplest transposition cipher
• Plaintext is written down as a sequence of diagonals and then
read off as a sequence of rows

• To encipher the message “meet me after the toga party” with a

rail fence of depth 2, we would write:
m e m a t r h t g p r y
e t e f e t e o a a t
Encrypted message is:
MEMATRHTGPRYETEFETEOAAT Decryption???
For the plaintext we used above, "defend the east wall", Homework
with a key of 3,
we get the encryption process shown below.
 Row Transposition Cipher
• Is a more complex transposition As an example, let's encrypt the
message "The tomato is a plant in
• Write the message in a rectangle, row by row, and the nightshade family" using the
read the message off, column by column, but permute keyword tomato. We get the grid
the order of the columns given below.

• The order of the columns then becomes the key to the

algorithm
Key: 4312 5 67
Plaintext: atta c kp
ostpone
dunt i l t
w o a mx y z
Ciphertext: TTNAAPTMTSUOAODWCOIXKNLYPETZ
Rotor Machines
Steganography
 • Character marking
• Selected letters of printed or
typewritten text are over-written in
Other pencil
• The marks are ordinarily not visible
Steganography unless the paper is held at an angle
to bright light
Techniques • Invisible ink
• A number of substances can be
used for writing but leave no visible
trace until heat or some chemical is
applied to the paper
• Pin punctures
• Small pin punctures on selected
letters are ordinarily not visible
unless the paper is held up in front
of a light
• Typewriter correction ribbon
• Used between lines typed with a
black ribbon, the results of typing
with the correction tape are visible
only under a strong light
 Summary
• Symmetric Cipher • Substitution
Model techniques
• Cryptography • Caesar cipher
• Cryptanalysis and • Monoalphabetic
Brute-Force Attack ciphers
• Playfair cipher
• Transposition
• Hill cipher
techniques
• Polyalphabetic ciphers
• Rotor machines • One-time pad

• Steganography