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
Academic Year: 2020 - 21

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 nondeterministic
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

Digit al Signat ure DSS/ SHA or
RSA/ SHA
Message CAST or I DEA or
Encrypt ion t hr ee-key t r iple DES
wit h Diffi e-Hellman
or RSA
Compression ZI P
E-mail Radix-64 conversion
Compat ibilit y
Segment at ion -
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
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)
.
. 1. Architecture: Architecture or IP Security
Architecture covers the general concepts, definitions,
protocols, algorithms, and security requirements of IP
Security technology.
2. ESP Protocol: ESP(Encapsulation Security Payload)
provides a confidentiality service. Encapsulation
Security Payload is implemented in either two ways:
• ESP with optional Authentication.
• ESP with Authentication
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
.
Next Header – Next Header is 8-bit field that identifies type of
header present after Authentication Header. In case of TCP, UDP or
destination header or some other extension header it will store
correspondence IP protocol number . Like, number 4 in this field
will indicate IPv4, number 41 will indicate IPv6 and number 6 will
indicate TCP.
Payload Length – Payload length is length of Authentication
header .Reserved – This is 16-bit field which is set to “zero” by
sender as this field is reserved for future use.
Security Parameter Index (SPI) – It is arbitrary 32-bit field.
It is very important field which identifies all packets which
belongs to present connection. If we’re sending data from
Source A to Destination B. Both A and B will already know
algorithm and key they are going to use.
Sequence Number – This unsigned 32-bit field contains counter
value that increases by one for each packet sent. Every packet will
need sequence number. It will start from 0 and will go till
 Authentication Data (Integrity Check Value) – Authentication
data is variable length field that contains Integrity Check Value
(ICV) for packet. Using hashing algorithm and secret key, sender
will create message digest which will be sent to receiver. Receiver
on other hand will use same hashing algorithm and secret key. If
both message digest matches then receiver will accept data.
 How Authentication Header can be useful?
• Message Integrity is also known as Connection-less Integrity
• Source Authentication
• Replay attack protection
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
• Security Parameter Index(SPI): This parameter is used by Security
Association. It is used to give a unique number to the connection built
between the Client and Server.
• Sequence Number: Unique Sequence numbers are allotted to every
packet so that on the receiver side packets can be arranged properly.
• Payload Data: Payload data means the actual data or the actual
message. The Payload data is in an encrypted format to achieve
confidentiality.
• Padding: Extra bits of space are added to the original message in
order to ensure confidentiality. Padding length is the size of the added
bits of space in the original message.
• Next Header: Next header means the next payload or next actual data.
• Authentication Data This field is optional in ESP protocol packet
format.
.
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
Internet Security Association and Key Management
Protocol (ISAKMP) is a framework for establishing
security associations (SAs) and performing key
exchange in a secure manner.
 SAS are agreements between two devices that define
how they will communicate securely. Key exchange
refers to the process of exchanging keys or other
cryptographic material that is used to secure
communication.
ISAKMP is a protocol that defines the structure and
format of messages used to establish and maintain Sas
ISAKMP is a protocol that defines the structure and
format of messages used to establish and maintain Sas
ISAKMP is used in conjunction with other protocols,
such as the Internet Key Exchange (IKE) protocol, which
is used to negotiate and establish SAs
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