Unit 4 Electronic Mail Security

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Electronic Mail Security

This section discusses two protocols providing


security services for e-mails:

1.Pretty Good Privacy (PGP) and

2. Secure/Multipurpose Internet Mail Extension


(S/MIME).

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qTo introduce “Internet security” at the
and two protocols, and , that
implement that idea.
qTo show how PGP and S/MIME can provide
and

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ü E-mail Security
ü Pretty Good Privacy (PGP)
ü Key Rings
ü PGP Certificates
ü S/MIME
ü Applications of S/MIME

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PEM Security Features
•Initially developed by IETF & Privacy Security Research
Group.

•Standard adopted by Internet Architecture Board.

Privacy Enhanced Mail (PEM)

Encryption Non- Message


repudiation integrity
PEM Operations

Architecture & OS
1. Canonical Conversion Uniform ,
Independent Format
2. Digital Signature MD, Kpvt

E-mail + DS
3. Encryption Symmetric key
DES & Its Variant

4. Base 64 encoding
Pretty Good Privacy (PGP)

• widely used de facto secure email

• developed by Phil Zimmermann

• Supports the basic requirements of cryptography.

• Simple to use

• Completely Free
PGP Security Features

Pretty Good Privacy


(PGP)

Non- Message
Encryption repudiation integrity
Note

In e-mail security, the sender of the


message needs to include the name
or identifiers of the algorithms
used in the message,along with the value
of key.

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PGP Algorithm
Algorithm Type Description

Asymetric Key RSA,DSS


Message Digest MD5,SHA-1,RIPE-MD
Encryption IDEA,DES-3,AES
PGP Operations

1. Digital Signature SHA-1

2. Compression Lempel-Ziv Algo

3. Encryption IDEA with CFB

4. Enveloping Symmetric key


encrypted with receivers
public key
5. Base 64 encoding
PGP Security Options
 While sending an E-mail Message following
Security Option can be choosen:

 Signature Only (Step 1 and 2)


 Signature and Base-64 encoding(Step 1,2 and 5)
 All 5 steps
Step 2: Lempel-Ziv Algorithm (Zip)

What is your name? My name is Atul. Original string

1. A = is 2. B = name Variable creation


and assignment

What 1 your 2? My 2 1 Atul. Compressed


string
Envelope

In e-mail security, the encryption/decryption


is done using a symmetric-key algorithm,
but the secret key to decrypt the message
is
encrypted with the public key of the
receiver and is sent with the message.

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Step 5:Base-64 Encoding Concept

01010101010101000011000101011111001001… Input bit stream Binary I/P

01010101… 00010101 … 00010101 … Divided into 24-bit


blocks

010101 010000 111110 001011 Each 24-bit divided into four 6-bit
blocks

01010110 01000011 11111010 00101100 6-bit block mapped to 8-bit


block Character O/P
base64_encoding_table.
PGP Operations
(MIME)
Multipurpose Internet Mail Extensions

 Traditional email communication is text-only

 Modern email communication demands multimedia


(sound, video, pictures, etc)

 Enhancements provided in the form of MIME


From: Atul Kahate <[email protected]>
To: Amit Joshi<[email protected]>
Subject: Cover image for the book
MIME-Version: 1.0
Content-Type: image/gif Mulimedia File
<Actual image data in the binary form such as R019a0asdjas0 …>
S/MIME Functionalities

• 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 Functionalities

Functionality Description

Enveloped data Consists of encrypted content of any type, and the encryption key encrypted
with the receiver’s public key.

Signed data Consists of a message digest encrypted with the sender’s private key. The
content and the digital signature are both Base-64 encoded.

Clear-signed data Similar to Signed data. However, only the digital signature is Base-64 encoded.

Signed and Signed-only and Enveloped-only entities can be combined, so that the
Enveloped data Enveloped data can be signed, or the Signed/Clear-signed data can be
enveloped.
The following shows an example of an enveloped-data in which
a small message is encrypted using triple DES.

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S/MIME Content Types

Type Sub-type Description

Multipart Signed A clear signed message consisting of the message


and the digital signature.
     

Application PKCS#7 MIME A signed MIME entity.


Signed Data

  PKCS#7 MIME An enveloped MIME entity.


Enveloped Data

  PKCS#7 MIME An entity that contains only digital certificates. No


Degenerate Signed
Data
Content
  PKCS#7 Signature The content type of the signature subpart of a
multipart/signed message.
  PKCS#10 MIME A certificate registration request.
S/MIME Additional Security Features
 SIGNED RECEIPTS:-
Acknowledgement
Proof of delivery
• SECURITY LABLE:-
Sensitivity
Access control
Priority
 SECURE MAILING LISTS:-
Mailing List Agent(MLA)
Used when their is N no. of Recipient
Sender MLA Receive
Figure 30.22 A plaintext message

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Figure 30.23 An authenticated message

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Figure 30.24 A compressed message

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Figure 30.25 A confidential message

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Figure 30.26 Key rings in PGP

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Note

In PGP, there can be multiple paths from


fully or partially trusted authorities
to any subject.

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Figure 30.27 Trust model

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Figure 30.28 Signed-data content type

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Figure 30.29 Encrypted-data content type

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Figure 30.30 Digest-data content type

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Figure 30.31 Authenticated-data content type

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