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EMAIL SECURITY
PGP Electronic Mail Security
Despite the refusal of VADM Poindexter and LtCol North to
appear, the Board's access to other sources of information filled much of this gap. The FBI provided documents taken from the files of the National Security Advisor and relevant NSC staff members, including messages from the PROF system between VADM Poindexter and LtCol North. The PROF messages were conversations by computer, written at the time events occurred and presumed by the writers to be protected from disclosure. In this sense, they provide a first-hand, contemporaneous account of events. —The Tower Commission Report to President Reagan on the Iran-Contra Affair, 1987 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 ➢ 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 Operation – Authentication 1. sender creates message 2. make SHA-1160-bit hash of message 3. attached RSA signed hash to message 4. receiver decrypts & recovers hash code 5. receiver verifies received message hash PGP Operation – Confidentiality 1. sender forms 128-bit random session key 2. encrypts message with session key 3. attaches session key encrypted with RSA 4. receiver decrypts & recovers 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 ➢ bydefault 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 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 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 PGP Key Rings 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 PGP Trust Model Example Summary ➢ have considered: ⚫ secure email ⚫ PGP
(New Horizons in Contemporary Writing) Erik Ketzan - Thomas Pynchon and The Digital Humanities - Computational Approaches To Style-Bloomsbury Academic (2021)