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Electronic mail security


Electronic mail security S/MIME Functions Enveloped Data: Encrypted content and encrypted session keys for recipients. Signed Data: Message Digest encrypted with ... – PowerPoint PPT presentation

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Title: Electronic mail security

Electronic mail security
  • Pretty good privacy
  • S/MIME

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

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
  • Philip R. Zimmerman is the creator of PGP.
  • PGP provides a confidentiality and authentication
    service that can be used for electronic mail and
    file storage applications.

  • PGP is a remarkable phenomenon that provides
    confidentiality, authentication, and compression
    for email and data storage.
  • Its building blocks are made of the best
    available cryptographic algorithms RSA, DSS,
  • It is independent of operating system and
  • It has a small set of easy-to-use commands

  • available on Unix, PC, Macintosh and Amiga
  • originally free, now have commercial versions
    available also

Why Is PGP Popular?
  • It is availiable free on a variety of platforms.
  • Based on well known algorithms.
  • Wide range of applicability
  • Not developed or controlled by governmental or
    standards organizations

Operational Description
  • Consist of five services
  • Authentication
  • Confidentiality
  • Compression
  • E-mail compatibility
  • Segmentation

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PGP Operation Authentication
  1. sender creates a message
  2. SHA-1 used to generate 160-bit hash code of
  3. hash code is encrypted with RSA using the
    sender's private key, and result is attached to
  4. receiver uses RSA or DSS with sender's public key
    to decrypt and recover hash code
  5. receiver generates new hash code for message and
    compares with decrypted hash code, if match,
    message is accepted as authentic

PGP Operation Confidentiality
  • sender generates message and random 128-bit
    number to be used as session key for this message
  • message is encrypted, using CAST-128 / IDEA/3DES
    with session key
  • session key is encrypted using RSA with
    recipient's public key, then attached to message
  • receiver uses RSA with its private key to decrypt
    and recover session key
  • session key is used to decrypt message

PGP Operation Confidentiality Authentication
  • uses both services on same message
  • create signature attach to message
  • encrypt both message signature
  • attach RSA 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
  • The placement of the compression algorithm is
  • 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
  • The scheme uses radix-64 algorithm
  • maps 3 bytes to 4 printable chars
  • also appends a CRC

E-mail Compatibility
  • The use of radix-64 expands the message by 33.

Segmentation and Reassembly
  • E-mail facilities are 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 to
  • The receiver strip of all e-mail headers and
    reassemble the block.

Summary of PGP Services
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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 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
  • Key ID of KUa public key is KUa mod 264
  • will very likely be unique
  • also use key ID in signatures

Format of PGP Message
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

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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

The Use of Trust
  • Key legitimacy field
  • Signature trust field
  • Owner trust field

See Table 15.2 (W. Stallings)
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Revoking Public Keys
  • The owner issue a key revocation certificate.
  • Normal signature certificate with a revote
  • Corresponding private key is used to sign the

  • Secure/Multipurpose Internet Mail Extension
  • S/MIME will probably emerge as the industry
  • PGP for personal e-mail security

Simple Mail Transfer Protocol (SMTP, RFC 822)
  • SMTP Limitations - Can not transmit, or has a
    problem with
  • executable files, or other binary files (jpeg
  • national language characters (non-ASCII)
  • messages over a certain size
  • ASCII to EBCDIC translation problems
  • lines longer than a certain length (76 characters)

Header fields in MIME
  • MIME-Version Must be 1.0 -gt RFC 2045, RFC
  • Content-Type Describes the data contained in
    the body . More types being added by developers
  • Content-Transfer-Encoding How message has been
    encoded (radix-64)
  • Content-ID Unique identifying character string.
  • Content Description Text description of the
    object with the body. Needed when content is not
    readable text (e.g.,audio data)

S/MIME Functions
  • Enveloped Data Encrypted content and encrypted
    session keys for recipients.
  • Signed Data Message Digest encrypted with
    private key of signer..Content signature is
    then encoded using base64.
  • Clear-Signed Data Only Digital Signature is
    encoded. Receiver can view msg content.
  • Signed and Enveloped Data Various orderings for
    encrypting and signing.

Algorithms Used
  • Message Digesting SHA-1 and MD5
  • Digital Signatures DSS RSA
  • Secret-Key Encryption(For message encryption)
    Triple-DES, RC2/40 (exportable)
  • Public-Private Key Encryption(For Session keys
    encryption) RSA with key sizes of 512 and 1024
    bits, and Diffie-Hellman.

S/MIME Certificate Processing
  • S/MIME uses X.509 v3 certificates
  • managed using a hybrid of a strict X.509 CA
    hierarchy PGPs web of trust
  • each client has a list of trusted CAs certs
  • and own public/private key pairs certs
  • certificates must be signed by trusted CAs

User Agent Role
  • S/MIME uses Public-Key Certificates - X.509
    version 3 signed by Certification Authority
  • Functions
  • Key Generation - Diffie-Hellman, DSS, and RSA
  • Registration - Public keys must be registered
    with X.509 CA.
  • Certificate Storage - Local (as in browser
    application) for different services.
  • Signed and Enveloped Data - Various orderings for
    encrypting and signing.

Certificate Authorities
  • have several well-known CAs
  • Verisign one of most widely used
  • Verisign issues several types of Digital IDs
  • with 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

User Agent Role
  • Example Verisign (www.verisign.com)
  • Class-1 Buyers email address confirmed by
    emailing vital info.
  • Class-2 Postal address is confirmed as well,
    and data checked against directories.
  • Class-3 Buyer must appear in person, or send
    notarized documents.
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