Mạng máy tính 1 - Chapter 6: Electronic mail security
Does not rely on certificate authorities
in PGP every user is own CA
▫ can sign keys for users they know directly
(certificates are like X.509)
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
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Chapter 6
Electronic Mail Security
MSc. NGUYEN CAO DAT
Dr. TRAN VAN HOAI
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Email Security
Email is one of the most widely used and
regarded network services
SMTP (Simple Mail Transfer Protocol)
▫ 25/TCP
▫ Commands, responses: ASCII
▫ Separate headers from envelope
▫ Binary content, structure
MIME (multipurpose internet mail extensions)
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Email Security
Mail servers & mail agents use SMTP for
exchange.
Email clients use SMTP typically for relaying
only, preferring POP/IMAP for receiving
Currently message contents are not secure :
▫ may be inspected either in transit
▫ or by suitably privileged users on destination
system
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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
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Email Security Approaches
Pretty Good Privacy (PGP)
▫ Personal e-mail security for many users
▫ Basic security services
Confidentiality service
Authentication service
S/MIME (Secure/Multipurpose Internet Mail Extension)
▫ A security enhancement to the MIME
▫ Industry standard for commercial and organizational
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Pretty Good Privacy (PGP)
widely used confidentiality and authentication
service for securing electronic mail and other
file storage applications
developed by Phil Zimmermann
selected best available crypto algorithms to use
integrated into a single program
available on Unix, PC, Macintosh systems
originally free, now have commercial versions
available also
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PGP Operational description
Consist of five services:
▫ Authentication
▫ Confidentiality
▫ Compression
▫ E-mail compatibility
▫ Segmentation
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PGP Operation – Authentication
1. sender creates message
2. Generates a digital signature for the message
3. use SHA-1 to generate 160-bit hash of
message
4. signed hash with RSA using sender's private
key, and is attached to message
5. receiver uses RSA with sender's public key to
decrypt and recover hash code
6. receiver verifies received message using hash
of it and compares with decrypted hash code
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PGP Operation – Authentication
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PRa = private key of user A, used in public-key encryption scheme
PUa=public key of user A, used in public-key encryption scheme
EP = public-key encryption
DP = public-key decryption
H = hash function
|| = concatenation
Z= compression using ZIP algorithm
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PGP Operation – Confidentiality
1. sender generates a message and encrypts it.
2. Generates a128-bit random number as session
key
3. Encrypts the message using CAST-128 / IDEA /
3DES in CBC mode with session key
4. session key encrypted using RSA with
recipient's public key and attached to the msg
5. receiver uses RSA with private key to decrypt
and recover session key
6. session key is used to decrypt message
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PGP Operation – Confidentiality
Ks
=session key used in symmetric encryption
scheme
Ks=session key used in symmetric encryption scheme
EC = symmetric encryption
DC = symmetric decryption
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PGP Operation – Confidentiality & Authentication
can use both services on the same message
▫ create signature & attach it to the message
▫ encrypt both message & signature
▫ attach RSA/ElGamal encrypted session key
This sequence is preferred because
▫ One can store the plaintext message/file and its signature
▫ no need to decrypt the message/file again and again
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PGP Operation – Confidentiality & Authentication
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PGP Operation – Compression
PGP compresses messages to save space for
e-mail transmission and storage
by default PGP compresses message after
signing but before encrypting
▫ so can store uncompressed message & signature for
later verification
▫ Encryption after compression strengthens security
(because compression has less redundancy)
uses ZIP compression algorithm
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PGP Operation – Email Compatibility
when using PGP will have binary data (8-bit
octets) 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
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Segmentation and reassembly
Often restricted to a maximum message length
of 50,000 octets
Longer messages must be broken up into
segments
PGP automatically subdivides a message that is
too large
The receiver strips off all e-mail headers and
reassemble the block
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PGP Operation – Summary
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PGP Services – Summary
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Function Algorithm Used
Digital Signature DSS/SHA or RSA/SHA
Message Encryption CAST or IDEA or three-
key triple DES with Diffie-
Hellman or RSA
Compression ZIP
E-mail Compatibility Radix-64 conversion
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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
-actual keys hit
-keystroke timing of a user
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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
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PGP Message Format
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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
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PGP Message Generation
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PGP Message Reception
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The main issue: PGP key management
does not rely on certificate authorities
in PGP every user is own CA
▫ can sign keys for users they know directly
(certificates are like X.509)
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
BK
TP.HCM
Summary
have considered:
▫ Email security
▫ PGP
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