X. 509 Authentication Service

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X.509 Authentication Service

ITU-T (International Telecommunication Union – Telecommunication Standardization Sector) recommendation X.509 is a part of the X.500 series of recommendations that define a directory service. The directory is a server or distributed set of servers that maintains a database of information about users. The information includes a mapping from user name to network address, as well as other attributes and information about the users.

X.509 defines a framework for the provision of authentication services by the X.500 directory to its users. The directory may serve as a repository of public-key certificates. Each certificate contains the public key of a user and is signed with the private key of a trusted certification authority. X.509 defines alternative authentication protocols based on the use of public-key certificates.

X.509 is an important standard because the certificate structure and authentication protocols defined in X.509 are used in variety of contexts (SSL, SET, etc.).

A third version of X.509 was issued in 1995 and revised in 2000.


The heart of X.509 scheme is the public-key certificate associated with each user. These user certificates are assumed to be created by some trusted certificate authority (CA) and placed in the directory by the CA or by the user. The directory itself is not responsible for the creation of public keys or for the certification function; it merely provides an easily accessible location for users to obtain certificates.

Figure 14.3a shows the general format of a certificate, which includes the following elements (www.dante.net/np/ds/osi/9594-8-X.509.A4.ps ):

Certificates (Cont 1)

  1. Version: Differentiates among successive versions of the certificate format: the default version is 1. If the Issuer Unique Identifier or Subject Unique Identifier are present, the value must be version 2. If one or more extensions are present, the version must be version 3.

  2. Serial number: An integer value, unique within the issuing CA, that is unambiguously associated with this certificate

  3. Signature algorithm identifier: The algorithm used to sign the certificate, together with any associated parameters. Because this information is repeated in the Signature field at the end of the certificate, this field has little, if any, utility

  4. Issuer name: X.500 name of the CA that created and signed this certificate (about X.500 names see, for example, http://java.sun.com/products/jndi/tutorial/ldap/models/x500.html )

  5. Period of validity: Consists of two dates: the first and the last on which certificate is valid

  6. Subject name: The name of the user to whom this certificate refers. That is, this certificate certifies the public key of the subject who holds the corresponding private key

  7. Subject’s public key information: The public key of the subject, plus an identifier of the algorithm for which this key is to be used, together with any associated parameters

  8. Issuer unique identifier: An optional bit string field used to identify uniquely the issuing CA in the event the X.500 name has been reused for different entities

  9. Subject unique identifier: An optional bit string used to identify uniquely the subject in the event the X.500 name has been reused for different entities

  10. Extensions: A set of one or more extension fields. Extensions were added in version 3 and are discussed later

  11. Signature: Covers all of the other fields of the certificate; it contains the hash code of the other fields, encrypted with the CA’s private key. This field includes the signature algorithm identifier

The unique identifier fields were added in version 2 to handle the possible reuse of subject and/or issuer names over time. These fields are rarely used.

The standard uses the following notation to define a certificate:



Y<> = certificate of user X issued by certification authority Y

Y{I} = the signing of I by Y. It consists of I with an encrypted hash code appended

The CA signs the certificate with its private key. If the corresponding public key is known to a user, then that user can verify that a certificate signed by the CA is valid.

Obtaining a User’s Certificate

User certificates generated by a CA have the following characteristics:

  1. Any user with access to the public of the CA can verify the user
    public key that was encrypted

  2. No party other than the CA can modify the certificate without this being detected

Because certificates are unforgeable, they can be placed in a directory without the need for the directory to make special efforts to protect them.

If all users subscribe to the same CA, then there is a common trust of that CA. All user certificates can be placed in the directory for access by all users. In addition, a user can transmit his certificate directly to other users. In either case, once B is in possession of A’s certificate, B has confidence that message it encrypts with A’s public key will be secure from eavesdropping and that messages signed with A’s private key are unforgeable.

If there is a large community of users, it may not be practical for all users to subscribe to the same CA. Because it is the CA that signs certificates, each participating user must have a copy of the CA’s own public key to verify signatures. This public key must be provided to each user in an absolutely secure (with respect to integrity and authenticity) way so that the user has confidence in the associated certificates. Thus, with many users, it may be more practical for there to be a number of CAs, each of which securely provides its public key to some fraction of the users.

Now suppose that A has obtained a certificate from certification authority X1 and B has obtained a certificate from CA X2. If A does not securely know the public key of X2, then B’s certificate, issued by X2, is useless to A. A can read B’s certificate, but A cannot verify the signature. However, if the two CAs have securely exchanged their own public keys, the following procedure will enable A to obtain B’s public key:

  1. A obtains from directory, the certificate of X2 signed by X1. Because A securely knows X1’s public key, A can obtain X2’s public key from its certificate and verify it by means of X1’s signature on the certificate

  2. A then goes back to the directory and obtains the certificate of B signed by X2. Because A now has a trusted copy of X2’s public key, A can verify the signature and securely obtain B’s public key

A has used a chain of certificates to obtain B’s public key. In the notation of X.509, this chain is expressed as


In the same fashion, B can obtain A’s public key with the chain:


This scheme need not be limited to a chain of two certificates. An arbitrarily long path of CAs can be followed to produce a chain. A chain with N elements would be expressed as


In this case, each pair of CAs in the chain (Xi, Xi+1) must have created certificates for each other.

All these certificates of CAs by CAs need to appear in the directory, and the user needs to know how they are linked to follow a path to another user’s public-key certificate. X.509 suggests that CAs are arranged in a hierarchy so that navigation is straightforward.

Figure 14.4, taken from X.509, is an example of such a hierarchy. The connected circles indicate the hierarchical relationship among the CAs; the associated boxes indicate certificates maintained in the directory for each CA entry. The directory entry for each CA includes two types of certificates:

  • Forward certificates: Certificates of X generated by other CAs

  • Reverse certificates: Certificates generated by X that are the certificates of other CAs

Obtaining a User’s Certificate (Cont 1)

In this example, user A can acquire the following certificates from the directory to establish a certification path to B:

X<> W<> V<> Y<> Z<>

When A has obtained these certificates, it can unwrap the certification path in sequence to recover a trusted copy of B’s public key. Using this public key, A can send encrypted messages to B. If A wishes to receive encrypted messages from B, or to sign messages sent to B, then B will require A’s public key, which can be obtained from the following certification path:

Z<> Y<> V<> W<> X<>

B can obtain this set of certificates from the directory, or A can provide them as part of its initial message to B.

Revocation of Certificates

Recall from Figure 14.3 that each certificate includes a period of validity. Typically, a new certificate is issued before the expiration of the old one. In addition, it may be desirable on occasion to revoke a certificate before it expires, for one of the following reasons:

  1. The user’s private key
    is assumed to be compromised

  2. The user is no longer certified by this CA

  3. The CA’s certificate is assumed to be compromised

Each CA must maintain a list consisting of all revoked but not expired certificates issued by that CA, including both those issued to users and to other CAs. These lists should be posted on the directory.

Each certificate revocation list (CRL) posted to the directory is signed by the issuer and includes (Figure 14.3b) the issuer’s name, the date the list was created, the date the next CRL is scheduled to be issued, and an entry for each revoked certificate. Each entry consists of the serial number of a certificate and revocation date for that certificate. Because serial numbers are unique within a CA, the serial number is sufficient to identify the certificate.

When a user receives a certificate in a message, the user must determine whether the certificate has been revoked. The user could check the directory each time a certificate is received. To avoid the delays (and possible costs) associated with directory searches, it is likely that the user would maintain a local cache of certificates and lists of revoked certificates.

Authentication Procedures

X.509 also includes three alternative authentication procedures that are intended for use across a variety of applications. All these procedures make use of public-key signatures. It is assumed that the two parties know each other’s public key, either by obtaining each other’s certificates from the directory or because the certificate is included in the initial message from each side. These procedures are treated as strong contrary to simple authentication procedures in which a client is authenticated to a server by sending him its identifier and password in clear or hashed together with a timestamp and nonce (www.dante.net/np/ds/osi/9594-8-X.509.A4.ps ):

Authentication Procedures (Cont 1)

Authentication Procedures (Cont 2)

One-Way Authentication

One way authentication involves a single transfer of information from one user (A) to another (B), and establishes the following:

  1. The identity of A and that the message was generated by A

  2. That the message was intended for B

  3. The integrity and originality (it has not been sent multiple times) of the message

Note that only the identity of the initiating entity is verified in this process, not that of the responding entity.

At minimum, the message includes a timestamp, , a nonce , and the identity of B and is signed with A’s private key. The timestamp consists of an optional generation time and an expiration time. This prevents delayed delivery of messages. The nonce can be used to detect replay attacks. The nonce value must be unique within the expiration time of the message. Thus, B can store the nonce

One-Way Authentication (Cont 1)

until it expires and reject any new messages with the same nonce.

For pure authentication, the message is used simply to present credentials to B. The message may also include information to be conveyed. This information, sgnData, is included within the scope of the signature, guaranteeing its authenticity and integrity. The message may also be used to convey a session key to B, encrypted with B’s public key.

Two-Way Authentication

In addition to the three elements just listed, two-way authentication establishes the following elements:

  1. The identity of B and that the reply message was generated by B

  2. That the message was intended for A

  3. The integrity and originality of the reply

The reply message includes the nonce from A, to validate the reply. It also includes a timestamp and nonce generated by B. As before, the message may include signed additional information and a session key encrypted with A’s public key.

Three-Way Authentication

Here, a final message from A to B is included, which contains a signed copy of the nonce . The intent of this design is that timestamps need not be checked: Because both nonces are echoed back by the other side, each side can check the returned nonce to detect replay attack. This approach is needed when synchronized clocks are not available. It is not shown in Figure 14.5, but the response from A also includes B to counter meet-in-the middle attack when opponent C intercepts messages between A and B

( http://nob.cs.ucdavis.edu/classes/ecs153-1997-01/Postscript/kerbiso.ps ).

Timestamps in the protocol above are zeros because in the three-way authentication clocks are not used.

One-Time Password (OTP)

We follow [L. Lamport, Password authentication with insecure communication. – Communications of ACM, 1981, v. 24, No 11, 770-772, http://cmpe.emu.edu.tr/chefranov/cmpe552-06/Lecture%20Notes/Lamport81.pdf ].

Passwords can be compromised when they cross a network or from a server’s database. In previous considerations, we assumed that there is a trusted third party and/or password database on the server side is safe. But this may not be true, and OTP schemas give solution for such cases.

Solution is strongly based on one-way hash functions.

Lamport’s schema allows having some finite number,, of authentications of a user to a server before the initialization procedure will be required. In initialization procedure, the user and server exchange securely secret information (by means of some special channel, personally, by ordered mail, courier, or in some other secure way). Schema assumes that a password never crosses insecure network, and the server’s password database might be compromised, but can’t be changed by an intruder. The server and user use one and the same hash function, , in the authentication procedure. The server authenticates the user applying the hash function to a current “password” value in its database. Actually, this value is derived from the password, and is used as a current password, which changes from one authentication to another. That’s why the schema is called “one-time password”. Current password depends on the authentication number and can’t exceed . OTP schemas represent “challenge-response” schemas.

Initialization Procedure

The client selects a password, , a number, , calculates




The client securely delivers to the server (, and the servers saves it into () tuple.

Authentication Procedure

When the client, C, requests authentication by the server, S, the following proceeds:
1. C -> S: C_ID //client sends his ID

2. S -> C: Counter(C_ID) //server responds by respective Counter value

3. C -> S: C_ID,

4. S: If then {

S authenticates C, and sets ()=()


Else C is not authenticated

After authentications, will become equal to one, and on the next authentication, C should pass his password in clear. Hence, maximal number of authentications without sending of the secret client’s password is . The trick with the schema is that due to one-wayness of the hash function, it is not feasible to find a value such that its hash will be equal to the stored by S value. As far as this value changes from one authentication to another, knowledge of the current password does not allow using it because rate of cracking may be less than that of password update. The schema has a problem that if is large (to avoid often initialization) then C should perform on average large amount of computations (Step 3 of authentication procedure)

MD5 Message Digest Algorithm

MD5 (http://www.faqs.org/rfcs/rfc1321.html ) was developed by Ron Rivest at MIT in 1991. Until 1996, when a flaw was found in it, MD5 was the most widely used secure hash algorithm. In description, we follow Stallings, Cryptography and Network Security textbook.

MD5 Logic

The algorithm takes as input a message of arbitrary length and produces as output a 128-bit message digest. The input is processed in 512-bit blocks.

Figure 12.1 depicts the overall processing of a message to produce a digest. The processing consists of the following steps:

  1. Append padding bits: The message is padded so that its length in bits is congruent to 448 modulo 512 (). That is, the length of the padded message is 64 bits less than an integer multiple of 512 bits. Padding is always added, even if the message is already of the desired length. For example, if the message is 448 bits long, it is padded with 512 bits to a length of 960 bits. Thus, the number of padding bits is in the range of 1 to 512. The padding consists of a single 1-bit followed by the necessary number of 0-bits.

  2. Append length: A 64-bit representation of the length in bits of the original message (before the padding) is appended to the result of Step 1 (least significant byte first). If the original

MD5 Logic (Cont 1)

length is greater than , then only the lower-order 64 bits of the length are used. Thus, the field contains the length of the original message, modulo .

The outcome of the first two steps yields a message that is an integer multiple of 512 bits in length. In Figure 12.1,

the expanded message is represented as the sequence of 512-bit blocks , so that the total length of the expanded message is bits. Equivalently, the result is a multiple of 16 32-bit words. Let M[0..N-1] denote the words of the resulting message with N an integer multiple of 16. Thus, .

  1. Initialize MD buffer: A 128-bit buffer is used to hold intermediate and final results of the hash function. The buffer can be represented as four 32-bit registers (A,B,C,D). These registers are initialized to the following 32-bit integers (hexadecimal values):





MD5 Logic (Cont 2)

These values are stored in little-endian format, which is the least-significant byte of a word in the low-address byte position. As 32-bit strings, the initialization values (in hexadecimal format) appear as follows:

Word A: 01 23 45 67

Word B: 89 AB CD EF

Word C: FE DC BA 98

Word D: 76 54 32 10

  1. Process message in 512-bit (16-word) blocks: The heart of the algorithm is a compression function that consists of four “rounds” of processing; this module is labeled in Figure 12.1, and its logic is illustrated in Figure 12.2. The four rounds have a similar structure, but each uses a different primitive logical function, referred to as F, G, H, and I in the specification.

Each round takes as input the current 512-bit block being processed () and the 128-bit buffer value ABCD and updates the contents of the buffer. Each round also makes use of one-fourth of a 64-element table T[1..64], constructed from the sine function. The i-th element of T, denoted

MD5 Logic (Cont 3)

T[i], has the value equal to the integer part of , where i is in radians. Because , each element of T is an integer that can be represented in 32 bits. The table provides a “randomized “ set of 32-bit patterns, which should eliminate any regularities in the input data. Table 12.1b lists values of T.

The output of the fourth round is added to the input to the first round () to produce . The addition is done independently for each of the four words in the buffer with each of the corresponding words in , using addition modulo .

  1. Output: After all L 512-bit blocks have been processed, the output from the L-th stage is the 128-bit message digest.

We can summarize the behavior of MD5 as follows:


- initial value of the ABCD buffer, defined in Step 3

- the q-th 512-bit block of the message

L – the number of blocks in the message (including padding and length fields)

- chaining variable processed with the q-th block of the message

- round function using primitive logic function x

- final message digest value

- addition modulo performed separately on each word of the pair of inputs

MD5 Logic (Cont 4)

MD5 Compression Function

Let’s look in more detail at the logic of the four rounds of the processing of one 512-bit block. Each round consists of a sequence of 16 steps operating on the buffer ABCD. Each step is of the form


a,b,c,d – the four words of the buffer, in a specified order that varies across steps

g – one of the primitive functions F,G,H,I

<< – circular left shift (rotation) of the 32-bit argument by s bits

X[k] – M[q16+k] – k-th 32-bit word in the q-th 512-bit of the message

T[i] – the i-th 32-bit word in matrix T

+ - addition modulo

Figure 12.3 illustrates the step operation

The order in which the four words (a,b,c,d) are used produces a word-level circular right shift for each step.

One of the four primitive logical functions is used for each of the four rounds of the algorithm. Each primitive function takes three 32-bit words as input and produces a 32-bit output. Each

MD5 Compression Function (Cont 1)

function performs a set of logical operations; that is, the n-th bit of the output is a function of the three inputs. The functions can be summarized as follows:


Primitive function g










Figure 12.4 adapted from RFC 1321, defines the processing algorithm of step 4. The array of 32-bit words X[0..15] holds the value of the current 512-bit input block being processed. Within a round, each of the 16 words of X[i] is used exactly once, during one step; the order in which these words are used varies from round to round. In the first round, they are used in the original order. The following permutations are defined for rounds 2 through 4:

Consider permutation:

































Each of the 64 32-bit word elements of T is used exactly once, during one step of one round. Also, note that for each step, only one of the 4 bytes of the ABCD buffer is updated. Hence, each byte of the buffer is updated four times during the round and then a final time at the end to produce the final output of this block. Finally, note that four different circular left shift amounts are used each round and are different from round to round. The point of all this complexity is to make it very difficult to generate collisions (two 512-bit blocks that produce the same output).

MD5 Compression Function (Cont 2)

We see that in Figure 12.4, order of k values in Round 2 follows specified above permutation .

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