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1 Pretty Good Privacy (PGP) Security for Electronic Email

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2 There are two main schemes which are especially designed to provide confidentiality and authentication for electronic mail systems. These are: PGP (Pretty Good Privacy) S/MIME (Secure/Multipurpose Internet Mail Extension)

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3 S/MIME S/MIME uses public key certificates conforming to standard X.509 and signed by a certification agency. In other respects, S/MIME is quite similar to PGP. S/MIME is not studied in any detail on this course and is not examinable. Details of the scheme are available in Chapter 5 of Stalling if you are interested.

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4 PGP Developed by Phil Zimmerman in 1995. Documentation and source code is freely available. The package is independent of operating system and processor. PGP does not rely on the establishment and its popularity and use have grown extensively since 1995.

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5 PGP combines the best available cryptographic algorithms to achieve secure e-mail communication. It is assumed that all users are using public key cryptography and have generated a private/public key pair. Either RSA (with RSA digital signatures) or El Gamel (with DSA) can be used. All users also use a symmetric key system such as triple DES or Rijndael.

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6 What does PGP do? PGP offers 5 services: 1.Authentication 2.Confidentiality 3.Compression 4.E-mail compatibility 5.Segmentation

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7 PGP Authentication This is a digital signature scheme with hashing. 1.Alice has (private/public) key pair (Ad/Ae) and she wants to send a digitally signed message m to Bob. 2.Alice hashes the message using SHA-1 to obtain SHA(m).

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8 3.Alice encrypts the hash using her private key Ad to obtain ciphertext c given by c=pk.encrypt Ad (SHA(m)) 4.Alice sends Bob the pair (m,c) 5.Bob receives (m,c) and decrypts c using Alice's public key Ae to obtain signature s s=pk.decrypt Ae (c)

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9 6.He computes the hash of m using SHA-1 and if this hash value is equal to s then the message is authenticated. Bob is sure that the message is correct and that is does come from Alice. Furthermore Alice cannot later deny sending the message since only Alice has access to her private key Ad which works in conjunction with the public key Ae.

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10 PGP Confidentiality 1.Alice wishes to send Bob a confidential message m. 2.Alice generates a random session key k for a symmetric cryptosystem. 3.Alice encrypts k using Bobs public key Be to get k = pk.encrypt Be (k)

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11 4.Alice encrypts the message m with the session key k to get ciphertext c c=sk.encrypt k (m) 5.Alice sends Bob the values (k,c) 6.Bob receives the values (k,c) and decrypts k using his private key B d to obtain k k=pk.decrypt Bd (k)

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12 7.Bob uses the session key k to decrypt the ciphertext c and recover the message m m=sk.decrypt k (c) Public and symmetric key cryptosystems are combined in this way to provide security for key exchange and then efficiency for encryption. The session key k is used only to encrypt message m and is not stored for any length of time.

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13 PGP Authenticaton and Confidentiality (at the same time ) The schemes for authentication and confidentiality can be combined so that Alice can sign a confidential message which is encrypted before transmission. The steps required are as follows: 1.Alice generates a signature c for her message m as in the Authentication scheme c=pk.encrypt Ad (SHA(m))

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14 2.Alice generates a random session key k and encrypts the message m and the signature c using a symmetric cryptosystem to obtain ciphertext C C=sk.encrypt k (m,c) 4.She encrypts the session key k using Bobs public key k = pk.encrypt Be (k) 5.Alice sends Bob the values (k,C)

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15 6.Bob recieves k and C and decrypts k using his private key Bd to obtain the session key k k=pk.decrypt Bd (k) 7.Bob decrypts the ciphertext C using the session key k to obtain m and c (m,c) = sk.decrypt k (C)

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16 8.Bob now has the message m. In order to authenticate it he uses Alices public key Ae to decrypt the signature c and hashes the message m using SHA-1. If SHA(m) = pk.decrypt Ae (c) Then the message is authenticated.

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17 PGP Compression PGP can also compress the message if desired. The compression algorithm is ZIP and the decompression algorithm is UNZIP. 1.The original message m is signed as before to obtain c=pk.encrypt Ad (SHA(m))

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18 2.Now the original message m is compressed to obtain M=ZIP(m) 3.Alice generates a session key k and encrypts the compressed message and the signature using the session key C=sk.encrypt k (M,c) 4.The session key is encrypted using Bobs public key as before.

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19 5.Alice sends Bob the encrypted session key and ciphertext C. 6.Bob decrypts the session key using his private key and then uses the session key to decrypt the ciphertext C to obtain M and c (M,c) = sk.decrypt k (C) 7.Bob decompresses the message M to obtain the original message m m=UNZIP(M)

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20 8.Now Bob has the original message m and signature c. He verifies the signature using SHA-1 and Alices public key as before. Note that the compression is applied after signing (due to implementation of ZIP) but before encryption (this strengthens the security of the scheme since the message has less redundancy after compression)

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21 PGP E-Mail Compatibility Many electronic mail systems can only transmit blocks of ASCII text. This can cause a problem when sending encrypted data since ciphertext blocks might not correspond to ASCII characters which can be transmitted. PGP overcomes this problem by using radix-64 conversion.

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22 Radix-64 conversion Suppose the text to be encrypted has been converted into binary using ASCII coding and encrypted to give a ciphertext stream of binary. Radix-64 conversion maps arbitrary binary into printable characters as follows:

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23 Radix-64 conversion 1.The binary input is split into blocks of 24 bits (3 bytes). 2.Each 24 block is then split into four sets each of 6-bits. 3.Each 6-bit set will then have a value between 0 and 2 6 -1 (=63). 4.This value is encoded into a printable character.

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24 6 bit value Character encoding 6 bit value Character encoding 6 bit value Character encoding 6 bit value Character encoding 0 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 ABCDEFGHIJKLMNOPABCDEFGHIJKLMNOP 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 QRSTUVWXYZabcdefQRSTUVWXYZabcdef 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 ghijklmnopqrstuvghijklmnopqrstuv 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 (pad) wxyz0123456789+/=wxyz0123456789+/=

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25 PGP Segmentation Another constraint of e-mail is that there is usually a maximum message length. PGP automatically blocks an encrypted message into segments of an appropriate length. On receipt, the segments must be re- assembled before the decryption process.

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26 Key Issues 1.Key Generation Recall that a new session key is required each time a message is encrypted. How are these keys generated? PGP uses the timing of key strokes and key patterns to generate random numbers.

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27 2.Key Identifiers PGP allows users to have more than one public/private key pair To increase security To ease the key changeover period So how does Bob know which set of keys he should be using?

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28 In the case of encryption, (Alice uses Bobs public key) Alice can send Bob the public key with the message since this is not secret (in fact Alice only sends the 64 least significant bits so that Bob can identify the key). In the case of digital signatures Alice uses her private key and Bob uses Alices corresponding public key. Alice cannot send Bob her private key, but she can look up the corresponding public key and send the 64 least significant bits of that.

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29 So a PGP message might consist of: Message component – the actual data to be transmitted + a filename + a timestamp; Signature component – timestamp + hash of message and timestamp + first part of message (so user can check that they are decrypting correctly) + Key ID of senders public key Session Key component – session key + key ID of recipients public key

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