PGP - Pretty Good Privacy

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1 I should be able to whisper something in your ear, even if your ear is 1000 miles away, and the government disagrees with that. -- Philip Zimmermann PGP - Pretty Good Privacy - services - message format - random number generation - key and trust mamagement

2 What is PGP? general purpose application to protect (encrypt and/or sign) files can be used to protect messages can be used by corporations as well as individuals based on strong cryptographic algorithms (IDEA, RSA, SHA-1) first version developed by Phil Zimmermann international version available free of charge at 2

3 PGP services messages authentication confidentiality compression compatibility segmentation and reassembly key management generation, distribution, and revocation of public/private keys generation and transport of session keys and IVs PGP services 3

4 Message authentication based on digital signatures supported algorithms: RSA/SHA and DSS/SHA K snd -1 sender m h σ hash hash enc enc PGP services receiver m h h σ hash hash compare compare dec dec accept / reject K snd 4

5 Message confidentiality symmetric key encryption in CFB mode with a random session key and IV session key and IV is encrypted with the public key of the receiver supported algorithms: symmetric: CAST, IDEA, 3DES asymmetric: RSA, ElGamal m prng prng K rcv {k, iv} Krcv sender s.enc s.enc k, iv a.enc a.enc PGP services {m} k 5

6 Compression applied after the signature enough to store clear message and signature for later verification it would be possible to dynamically compress messages before signature verification, but then all PGP implementations should use the same compression algorithm however, different PGP versions use slightly different compression algorithms applied before encryption would be useless after encryption compression reduces redundancy makes cryptanalysis harder supported algorithm: ZIP PGP services 6

7 compatibility encrypted messages and signatures may contain arbitrary octets most systems support only ASCII characters PGP converts an arbitrary binary stream into a stream of printable ASCII characters radix 64 conversion: 3 8-bit blocks 4 6-bit blocks PGP services 7

8 Radix 64 conversion table PGP services 6-bit character 6-bit character 6-bit character 6-bit character value encoding value encoding value encoding value encoding 0 A 16 Q 32 g 48 w 1 B 17 R 33 h 49 x 2 C 18 S 34 i 50 y 3 D 19 T 35 j 51 z 4 E 20 U 36 k F 21 V 37 l G 22 W 38 m H 23 X 39 n I 24 Y 40 o J 25 Z 41 p K 26 a 42 q L 27 b 43 r M 28 c 44 s N 29 d 45 t O 30 e 46 u P 31 f 47 v 63 / (pad) = 8

9 Combining services X := := file file signature? signature? no yes generate generate signature signature X := := s(x) s(x) X compress compress X := := Z(X) Z(X) encryption? encryption? yes generate generate envelop envelop X := :={iv, {iv, k} k} Krcv Krcv {X} {X} k k PGP services no radix radix X := := R64(X) R64(X) 9

10 General PGP message format session key component signature key ID of K rcv session key k and iv timestamp key ID of K snd leading two octets of hash { } Krcv hash(timestamp, data) { } Ksnd -1 filename time of creation ZIP { } k R64 PGP message format message data 10

11 Key IDs a user may have several public key private key pairs which private key to use to decrypt the session key? which public key to use to verify a signature? transmitting the whole public key would be wasteful associating a random ID to a public key would result in management burden PGP key ID: least significant 64 bits of the public key unique within a user with very high probability PGP message format 11

12 Random numbers in PGP pseudo-random numbers generated by a PRNG used as session keys and IVs true random numbers provide the initial seed for the PRNG provide additional input during pseudo-random number generation used to generate public key private key pairs PGP random number generation 12

13 The true random pool PGP maintains a 640-byte pool of random bits and a 64 byte key variable new random samples are obtained from keystroke timings and mouse movement and mixed into the pool as follows: each new random byte is XORed into the key variable currentpos old key variable PGP random number generation once enough new bytes have been added to the key, it is used to encrypt the pool in a message digest cipher configuration in CBC mode new random byte new key variable old pool 20 bytes (160 bits) key 64 bytes (512 bits) new pool after 1 step h currentpos h is the compression function of SHA-1 13

14 Generation of session keys and IVs rkey dtbuf (current time) E E PGP random number generation rseed true random bits E E + E E E E E + E IV[0..7] K[8..15] K[0..7] the PRNG is based on X9.17 extended with a pre-wash and a post-wash operation (see next slide) instead of 3DES, PGP uses CAST-128 E + E rseed* 14

15 Generation of session keys and IVs PGP random number generation pre-wash take the hash of the message this has already been generated if the message is being signed otherwise the first 4K of the message is hashed use the result as a key, use a null IV, and encrypt [rkey, rseed] in CFB mode if [rkey, rseed] is empty, it is filled up with true random bits from the random pool set [rkey, rseed] to the result of the encryption post-wash generate 24 more bytes as before but without XORing in true random bytes encrypt the result in CFB mode using K and IV set [rkey, rseed] to the result of the encryption 15

16 Private-key ring PGP key and trust management used to store the public key private key pairs owned by a given user essentially a table, where each row contains the following entries: timestamp key ID (indexed) public key encrypted private key user ID (indexed) passphrase hash hash enc enc private key encrypted private key 16

17 Public-key ring PGP key and trust management used to store public keys of other users a table, where each row contains the following entries: timestamp key ID (indexed) public key user ID (indexed) owner trust signature(s) signature trust(s) key legitimacy 17

18 Trust management PGP key and trust management owner trust assigned by the user possible values: unknown user usually not trusted to sign usually trusted to sign always trusted to sign ultimately trusted (own key, present in private key ring) signature trust assigned by the PGP system if the corresponding public key is already in the public-key ring, then its owner trust entry is copied into signature trust otherwise, signature trust is set to unknown user 18

19 Trust management PGP key and trust management key legitimacy computed by the PGP system if at least one signature trust is ultimate, then the key legitimacy is 1 (complete) otherwise, a weighted sum of the signature trust values is computed always trusted signatures has a weight of 1/X usually trusted signatures has a weight of 1/Y X, Y are user-configurable parameters example: X=2, Y=4 1 ultimately trusted, or 2 always trusted, or 1 always trusted and 2 usually trusted, or 4 usually trusted signatures are needed to obtain full legitimacy 19

20 Example key legitimacy X = 1, Y = 2 G C H B D user PGP key and trust management untrusted / usually untrusted usually trusted always trusted ultimately trusted (you) signature legitimate F A E L J I M K 20

21 Public-key revocation PGP key and trust management why to revoke a public key? suspected to be compromised (private key got known by someone) re-keying the owner issues a revocation certificate has a similar format to normal public-key certificates contains the public key to be revoked signed with the corresponding private key and disseminates it as widely and quickly as possible if a key is compromised: e.g., Bob knows the private key of Alice Bob can issue a revocation certificate to revoke the public key of Alice even better for Alice 21

22 Recommended readings Philip Zimmermann on PGP (part of the documentation that comes with the software) docs and faqs on 22

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