Cryptography and Network

Security

Chapter 15
 Chapter 15 – Electronic Mail Security

Despite the refusal of VADM Poindexter and LtCol North to

appear, the Board's access to other sources of information
filled much of this gap. The FBI provided documents taken
from the files of the National Security Advisor and relevant
NSC staff members, including messages from the PROF system
between VADM Poindexter and LtCol North. The PROF
messages were conversations by computer, written at the
time events occurred and presumed by the writers to be
protected from disclosure. In this sense, they provide a first-
hand, contemporaneous account of events.
—The Tower Commission Report to President Reagan on the
Iran-Contra Affair, 1987
 Email Security
• email is one of the most widely used and
regarded network services
• currently message contents are not secure
– may be inspected either in transit
– or by suitably privileged users on destination
system
 Email Security Enhancements
• confidentiality
– protection from disclosure
• authentication
– of sender of message
• message integrity
– protection from modification
• non-repudiation of origin
– protection from denial by sender
 Pretty Good Privacy (PGP)
• widely used de facto secure email
• developed by Phil Zimmermann
• selected best available crypto algs to use
• integrated into a single program
• on Unix, PC, Macintosh and other systems
• originally free, now also have commercial
versions available
 Review
• Kerberos Realms
 Review
• X.509 Authentication Service
– distributed servers maintaining user info database
– defines framework for authentication services
• directory may store public-key certificates
• with public key of user signed by certification authority
Review
 Review
• X.509 Authentication Protocols
 Email Security
• confidentiality
– protection from disclosure
• authentication
– of sender of message
• message integrity
– protection from modification
• non-repudiation of origin
– protection from denial by sender
PGP
Summary of PGP Services
 PGP Operation – Authentication
1. sender creates message
2. use SHA-1 to generate 160-bit hash of
message
3. signed hash with RSA using sender's private
key, and is attached to message
4. receiver uses RSA with sender's public key to
decrypt and recover hash code
5. receiver verifies received message using hash
of it and compares with decrypted hash code
 PGP Operation – Confidentiality
1. sender generates message and 128-bit
random number as session key for it
2. encrypt message using CAST-128 / IDEA /
3DES in CBC mode with session key
3. session key encrypted using RSA with
recipient's public key, & attached to msg
4. receiver uses RSA with private key to decrypt
and recover session key
5. session key is used to decrypt message
 PGP Operation – Confidentiality &
Authentication
• can use both services on same message
– create signature & attach to message
– encrypt both message & signature
– attach RSA/ElGamal encrypted session key
 PGP Operation – Compression
• by default PGP compresses message after
signing but before encrypting
– so can store uncompressed message & signature
for later verification
– & because compression is non deterministic
• uses ZIP compression algorithm
 PGP Operation – Email Compatibility
• when using PGP will have binary data to send
(encrypted message etc)
• however email was designed only for text
• hence PGP must encode raw binary data into
printable ASCII characters
• uses radix-64 algorithm
– maps 3 bytes to 4 printable chars
– also appends a CRC
• PGP also segments messages if too big
PGP Operation – Summary
 PGP Session Keys
• need a session key for each message
– of varying sizes: 56-bit DES, 128-bit CAST or IDEA,
168-bit Triple-DES
• generated using ANSI X12.17 mode
• uses random inputs taken from previous uses
and from keystroke timing of user
 PGP Public & Private Keys
• since many public/private keys may be in use, need
to identify which is actually used to encrypt session
key in a message
– could send full public-key with every message
– but this is inefficient
• rather use a key identifier based on key
– is least significant 64-bits of the key
– will very likely be unique
• also use key ID in signatures
PGP Message Format
 PGP Key Rings
• each PGP user has a pair of keyrings:
– public-key ring contains all the public-keys of
other PGP users known to this user, indexed by
key ID
– private-key ring contains the public/private key
pair(s) for this user, indexed by key ID & encrypted
keyed from a hashed passphrase
• security of private keys thus depends on the
pass-phrase security
Key Rings
PGP Message Generation
PGP Message Reception
 PGP Key Management
• rather than relying on certificate authorities
• in PGP every user is own CA
– can sign keys for users they know directly
• forms a “web of trust”
– trust keys have signed
– can trust keys others have signed if have a chain of
signatures to them
• key ring includes trust indicators
• users can also revoke their keys
Trust Flag
Web of Trust
Review
Review
Review
 Revoke a Public Key
• Why to Revoke?
• How to Revoke?
• Who can Revoke?
 S/MIME
• Secure/Multipurpose Internet Mail Extension
– Based on MIME
– RFC 822
• Text only
– MIME
• provided support for varying content types and multi-
part messages
• with encoding of binary data to textual form
 RFC 822
• Header
– Date:
– From:
– Subject:
– To:
– Cc:
– Bcc:
• Empty line
• Content
MIME
MIME
 S/MIME (Secure/Multipurpose Internet
Mail Extensions)
• security enhancement to MIME email
– S/MIME added security enhancements
• have S/MIME support in many mail agents
– eg MS Outlook, Mozilla, Mac Mail etc
 S/MIME Functions
• enveloped data
– encrypted content and associated keys
• signed data
– encoded message + signed digest
• clear-signed data
– cleartext message + encoded signed digest
• signed & enveloped data
– nesting of signed & encrypted entities
 S/MIME Cryptographic Algorithms
• digital signatures: DSS & RSA
• hash functions: SHA-1 & MD5
• session key encryption: ElGamal & RSA
• message encryption: AES, Triple-DES, RC2/40
and others
• MAC: HMAC with SHA-1
• have process to decide which algs to use
 S/MIME Messages
• S/MIME secures a MIME entity with a
signature, encryption, or both
• forming a MIME wrapped PKCS object
• have a range of content-types:
– enveloped data
– signed data
– clear-signed data
– registration request
– certificate only message
 S/MIME Certificate Processing
• S/MIME uses X.509 v3 certificates
• managed using a hybrid of a strict X.509 CA
hierarchy & PGP’s web of trust
• each client has a list of trusted CA’s certs
• and own public/private key pairs & certs
• certificates must be signed by trusted CA’s
 Certificate Authorities
• have several well-known CA’s
• Verisign one of most widely used
• Verisign issues several types of Digital IDs
• increasing levels of checks & hence trust
Class Identity Checks Usage
1 name/email check web browsing/email
2 + enroll/addr check email, subs, s/w validate
3 + ID documents e-banking/service access
 Summary
• have considered:
– secure email
– PGP
– S/MIME