LAKIREDDY BALI REDDY COLLEGE OF ENGINEERING

(AUTONOMOUS)
Accredited by NAAC & NBA (Under Tier - I) ISO 9001:2015 Certified Institution
Approved by AICTE, New Delhi. and Affiliated to JNTUK, Kakinada
L.B. REDDY NAGAR, MYLAVARAM, KRISHNA DIST., A.P.-521 230.
DEPARTMENT OF COMPUTER SCIENCE & ENGINEERING

17CI20 – INFORMATION SECURITY

Program & Semester: B.Tech & VII SEM
Section: CSE-A/B
Academic Year: 2021 - 22

EMAIL PRIVACY
By
Mr. Ch. Srinivasa Rao
Assistant Professor
Dept.of CSE, LBRCE
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

PGP provides a confidentiality and authentication service
that can be used for electronic mail and file storage
applications
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
PGP
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
Summary of PGP Services

Function Algorithm Used

Digital Signature DSS/SHA or
RSA/SHA
Message CAST or IDEA or
Encryption three-key triple DES
with Diffie-Hellman
or RSA
Compression ZIP
E-mail Radix-64 conversion
Compatibility
Segmentation -
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 key rings:
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 terms

• Timestamp: The date/time when this key pair was

generated.
• Key ID: The least significant 64 bits of the public key
for this entry.
• Public Key: The public-key portion of the pair.
• Private key: The private-key portion of the pair.
• User ID: Typically a user’s e-mail address.
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
Example

Email message: new

ASCII format:01101110 01100101 01110111
After encryption:10010001 10011010 10001000
Three bytes do not represent in any K.B ASCII chars most
email sys can not transmit& process piece of PT
Radix 64 conversion
The 24 bit block: 10010001 10011010 10001000
 four 64-bit block:100100 011001 101010 001000
Integer version : 36 25 38 8
Printable version: K Z M I
PGP is converting raw 8-bit binary stream to stream of
printable ASCII characters
S/MIME (Secure/Multipurpose Internet
Mail Extensions)
security enhancement to MIME email
original Internet RFC822 email was text only
MIME provided support for varying content types and
multi-part messages
with encoding of binary data to textual form
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
IP Security
have a range of application specific security
mechanisms
eg. S/MIME, PGP, Kerberos, SSL/HTTPS
however there are security concerns that cut across
protocol layers
would like security implemented by the network for
all applications
IPsec

general IP Security mechanisms

provides
authentication
confidentiality
key management
applicable to use over LANs, across public & private
WANs, & for the Internet
IPsec Uses
Benefits of IPsec
in a firewall/router provides strong security to all
traffic crossing the perimeter
in a firewall/router is resistant to bypass
is below transport layer, hence transparent to
applications
can be transparent to end users
can provide security for individual users
secures routing architecture
IP Security Architecture
specification is quite complex
defined in numerous RFC’s
incl. RFC 2401/2402/2406/2408
many others, grouped by category
mandatory in IPv6, optional in IPv4
have two security header extensions:
Authentication Header (AH)
Encapsulating Security Payload (ESP)
IPsec Services
Access control
Connectionless integrity
Data origin authentication
Rejection of replayed packets
a form of partial sequence integrity
Confidentiality (encryption)
Limited traffic flow confidentiality
Security Associations
a one-way relationship between sender & receiver that
affords security for traffic flow
defined by 3 parameters:
Security Parameters Index (SPI)
IP Destination Address
Security Protocol Identifier
has a number of other parameters
seq no, AH & EH info, lifetime etc
have a database of Security Associations
Authentication Header (AH)
provides support for data integrity & authentication of
IP packets
end system/router can authenticate user/app
prevents address spoofing attacks by tracking sequence
numbers
based on use of a MAC
HMAC-MD5-96 or HMAC-SHA-1-96
parties must share a secret key
Authentication Header
Transport & Tunnel Modes
Encapsulating Security Payload (ESP)

provides message content confidentiality &

limited traffic flow confidentiality
can optionally provide the same authentication
services as AH
supports range of ciphers, modes, padding
incl. DES, Triple-DES, RC5, IDEA, CAST etc
CBC & other modes
padding needed to fill blocksize, fields, for traffic flow
Encapsulating Security Payload
Transport vs Tunnel Mode ESP
transport mode is used to encrypt & optionally
authenticate IP data
data protected but header left in clear
can do traffic analysis but is efficient
good for ESP host to host traffic
tunnel mode encrypts entire IP packet
add new header for next hop
good for VPNs, gateway to gateway security
Combining Security Associations
SA’s can implement either AH or ESP
to implement both need to combine SA’s
form a security association bundle
may terminate at different or same endpoints
combined by
 transport adjacency
 iterated tunneling

issue of authentication & encryption order

Combining Security Associations
Key Management

handles key generation & distribution

typically need 2 pairs of keys
2 per direction for AH & ESP
manual key management
Sys admin manually configures every system
automated key management
automated system for on demand creation of keys for
SA’s in large systems
has Oakley & ISAKMP elements
Oakley
a key exchange protocol
based on Diffie-Hellman key exchange
adds features to address weaknesses
cookies, groups (global params), nonces, DH key
exchange with authentication
can use arithmetic in prime fields or elliptic curve
fields
ISAKMP
Internet Security Association and Key Management
Protocol
provides framework for key management
defines procedures and packet formats to establish,
negotiate, modify, & delete SAs
independent of key exchange protocol, encryption alg,
& authentication method
ISAKMP
ISAKMP Payloads & Exchanges
have a number of ISAKMP payload types:
Security, Proposal, Transform, Key, Identification,
Certificate, Certificate, Hash, Signature, Nonce,
Notification, Delete
 ISAKMP has framework for 5 types of message
exchanges:
base, identity protection, authentication only,
aggressive, informational
What are encryption ciphers? And what are
cipher suites?
 Cipher suites
Ciphers are algorithms, more specifically they’re a set
of steps for performing a cryptographic function
 – it can be encryption, decryption, hashing or
digital signatures.
Nowadays ciphers are dependent upon the advanced
processing capabilities of computers.
 One of the first, well-known historical ciphers
belonged to Caesar
 – the very first emperor of Rome and purveyor of
fancy appetizer salads –
- who used it to communicate with his generals
during military operations.
Cipher suites
Over the years, ciphers have become more complex,
 but the logic behind them has stayed the same
Whether it was Caesar crossing the Rubicon, the infamous
Enigma cipher of World War II
or some of the algorithms of today—the idea has always
been to encode or encipher a message in such a way that only
the intended party can read it.
Today we’re going to discuss SSL/TLS Cipher Suites –
groups of ciphers that help secure an HTTPS connection –
then go over their various parts and finish by looking at
what’s changed between TLS 1.2 and TLS 1.3.
Let’s hash it out.
 Cipher suites…
Cipher is really just an algorithm, or a set of steps that are used to
perform a specific mathematical function
– be that encryption, hashing or digital signatures.
 Ciphers have always had a basis in math,
 even Caesar’s primitive shift cipher required counting forward a
designated number of spaces in the alphabet to encrypt something.
I’m going to use Caesar’s cipher to explain some basic concepts that
will be useful later when we get into modern cipher suites.
 The piece of data or information – it’s all digital now, though
historically there’s typically been some kind of ink and
paper/parchment involved.
 Original unencrypted piece of data would be referred to as the
plaintext, as it’s easily readable in its raw form.
 After the encryption process has been performed, it becomes a piece
of cipher text
and should ideally be unreadable to anyone without the private key.
 Keys vs. Algorithms

 Encryption is performed by keys, but it’s important to square how keys and
algorithms/ciphers fit together.

 The algorithm or cipher used is just that, it’s a sequence of steps that must be used
to encrypt the plaintext.

 Depending on the cryptosystem, either the values within that algorithm, or the
value the algorithm arrives at itself, are the keys.
 We’ll clarify that point in a minute, just think of it this way: the algorithms are the
general principles/rules used by a given cryptosystem, the keys are what actually
performs the function
Summary

have considered:
IPsec security framework
AH
ESP
key management & Oakley/ISAKMP
Cryptographic suites