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Chapter: Cryptography and Network Security

Electronic Mail Security

1 PRETTY GOOD PRIVACY (PGP) 2. PGP Operation Summary: 3. The general structures of the private and public key rings are shown below:





PGP provides the confidentiality and authentication service that can be used for electronic mail and file storage applications. The steps involved in PGP are:


o   Select the best available cryptographic algorithms as building blocks.  


o   Integrate these algorithms into a general purpose application that is independent of operating system and processor and that is based on a small set of easy-to-use commands.  


o   Make the package and its documentation, including the source code, freely available via the internet, bulletin boards and commercial networks.  


o   Enter into an agreement with a company to provide a fully compatible, low cost commercial version of PGP.  


PGP has grown explosively and is now widely used. A number of reasons can be cited for this growth.


o   It is available free worldwide in versions that run on a variety of platform.  


o   It is based on algorithms that have survived extensive public review and are considered extremely secure.  


o   e.g., RSA, DSS and Diffie Hellman for public key encryption CAST-128, IDEA and 3DES for conventional encryption SHA-1 for hash coding.  


o   It has a wide range of applicability.  


o   It was not developed by, nor it is controlled by, any governmental or standards organization.  


Operational description


The actual operation of PGP consists of five services: authentication, confidentiality, compression, e-mail compatibility and segmentation.


1. Authentication


The sequence for authentication is as follows:


§  The sender creates the message  


§  SHA-1 is used to generate a 160-bit hash code of the message  


§  The hash code is encrypted with RSA using the sender‟s private key and the result is prepended to the message  


§  The receiver uses RSA with the sender‟s public key to decrypt and recover the hash code.  


·        The receiver generates a new hash code for the message and compares it with the decrypted hash code. If the two match, the message is accepted as authentic.


2. Confidentiality

Confidentiality is provided by encrypting messages to be transmitted or to be stored locally as files. In both cases, the conventional encryption algorithm CAST-128 may be used. The 64-bit cipher feedback (CFB) mode is used.


In PGP, each conventional key is used only once. That is, a new key is generated as a random 128-bit number for each message. Thus although this is referred to as a session key, it is in reality a one time key. To protect the key, it is encrypted with the receiver‟s public key.


The sequence for confidentiality is as follows:


o  The sender generates a message and a random 128-bit number to be used as a session key for this message only.  


o  The message is encrypted using CAST-128 with the session key.  


o  The session key is encrypted with RSA, using the receiver‟s public key and is prepended to the message.  


o  The receiver uses RSA with its private key to decrypt and recover the session key.  


o  The session key is used to decrypt the message.  


Confidentiality and authentication


Here both services may be used for the same message. First, a signature is generated for the plaintext message and prepended to the message. Then the plaintext plus the signature is encrypted using CAST-128 and the session key is encrypted using RSA.


3. Compression


As a default, PGP compresses the message after applying the signature but before encryption. This has the benefit of saving space for both e-mail transmission and for file storage.


The signature is generated before compression for two reasons:


o   It is preferable to sign an uncompressed message so that one can store only the uncompressed message together with the signature for future verification. If one signed a compressed document, then it would be necessary either to store a compressed version of the message for later verification or to recompress the message when verification is required.


o   Even if one were willing to generate dynamically a recompressed message fro verification, PGP‟s compression algorithm presents a difficulty. The algorithm is not deterministic; various implementations of the algorithm achieve different tradeoffs in running speed versus compression ratio and as a result, produce different compression forms.


Message encryption is applied after compression to strengthen cryptographic security. Because the compressed message has less redundancy than the original plaintext, cryptanalysis is more difficult. The compression algorithm used is ZIP.


4. e-mail compatibility


Many electronic mail systems only permit the use of blocks consisting of ASCII texts. To accommodate this restriction, PGP provides the service of


converting the raw 8-bit binary stream to a stream of printable ASCII characters. The scheme used for this purpose is radix-64 conversion. Each group of three octets of binary data is mapped into four ASCII characters.


e.g., consider the 24-bit (3 octets) raw text sequence 00100011 01011100 10010001, we can express this input in block of 6-bits to produce 4 ASCII characters.



5. Segmentation and reassembly


E-mail facilities often are restricted to a maximum length. E.g., many of the facilities accessible through the internet impose a maximum length of 50,000 octets. Any message longer than that must be broken up into smaller segments, each of which is mailed separately.


To accommodate this restriction, PGP automatically subdivides a message that is too large into segments that are small enough to send via e-mail. The segmentation is done after all the other processing, including the radix-64 conversion. At the receiving end, PGP must strip off all e-mail headers and reassemble the entire original block before performing the other steps.


2. PGP Operation Summary:



Cryptographic keys and key rings


Three separate requirements can be identified with respect to these keys:


A means of generating unpredictable session keys is needed.  


It must allow a user to have multiple public key/private key pairs.  


Each PGP entity must maintain a file of its own public/private key pairs as well as a file of public keys of correspondents.  


We now examine each of the requirements in turn.


1. Session key generation


Each session key is associated with a single message and is used only for the purpose of encryption and decryption of that message. Random 128-bit numbers are generated using CAST-128 itself. The input to the random number generator consists of a 128-bit key and two 64-bit blocks that are treated as plaintext to be encrypted. Using cipher feedback mode, the CAST-128 produces two 64-bit cipher text blocks, which are concatenated to form the 128-bit session key. The plaintext input to CAST-128 is itself derived from a stream of 128-bit randomized numbers. These numbers are based on the keystroke input from the user.


2. Key identifiers


If multiple public/private key pair are used, then how does the recipient know which of the public keys was used to encrypt the session key? One simple solution would be to transmit the public key with the message but, it is unnecessary wasteful of space. Another solution would be to associate an identifier with each public key that is unique at least within each user.


The solution adopted by PGP is to assign a key ID to each public key that is, with very high probability, unique within a user ID. The key ID associated with each public key consists


of its least significant 64 bits. i.e., the key ID of public key KUa is


(KUa mod 264).



message consists of three components.


Message component includes actual data to be transmitted, as well as the filename and a timestamp that specifies the time of creation.  


Signature component includes the following  


o   Timestamp time at which the signature was made.

o   o Message digest hash code.


o   Two octets of message digest – to enable the recipient to determine if the correct public key was used to decrypt the message.


o   Key ID of sender‟s public key – identifies the public key


Session key component includes session key and the identifier of the recipient public key.


3. Key rings


PGP provides a pair of data structures at each node, one to store the public/private key pair owned by that node and one to store the public keys of the other users known at that node. These data structures are referred to as private key ring and public key ring.


3. The general structures of the private and public key rings are shown below:


Timestamp the date/time when this entry was made.


Key ID the least significant bits of the public key.


Public key – public key portion of the pair.


Private key private key portion of the pair.


User ID the owner of the key.


Key legitimacy field indicates the extent to which PGP will trust that this is a valid public key for this user.


Fig. General Structure of Private and Public Rings


Signature trust field – indicates the degree to which this PGP user trusts the signer to certify


public key.


Owner trust field indicates the degree to which this public key is trusted to sign other public key




PGP message generation


First consider message transmission and assume that the message is to be both signed and encrypted. The sending PGP entity performs the following steps:



1. Signing the message


o   PGP retrieves the sender‟s private key from the private key ring using user ID as an index.


o   If user ID was not provided, the first private key from the ring is retrieved.  


o   PGP prompts the user for the passpharse (password) to recover the unencrypted private key.  


o   The signature component of the message is constructed.  


2. Encrypting the message


o   PGP generates a session key and encrypts the message.  


o   PGP retrieves the recipient‟s public key from the public key ring using user ID as index.  


o   The session key component of the message is constructed.  


The receiving PGP entity performs the following steps


1. Decrypting the message


o   PGP retrieves the receiver‟s private key from the private key ring, using the key ID field in the session key component of the message as an index.  


o   PGP prompts the user for the passpharse (password) to recover the unencrypted private key.  


o   PGP then recovers the session key and decrypts the message.  


2. Authenticating the message


o   PGP retrieves the sender‟s public key from the public key ring, using the key ID field in the signature key component of the message as an index.  


o   PGP recovers the transmitted message digest.  


o   PGP computes the message digest for the received message and compares it to the transmitted message digest to authenticate.

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