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5. More on Certificate Authentication

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5.1 The X.509 Trust Model

The X.509 protocols rely on a hierarchical trust model. In this trust model Certification Authorities (CAs) are used to certify entities. Usually more than one certification authorities exist, and certification authorities may certify other authorities to issue certificates as well, following a hierarchical model.


One needs to trust one or more CAs for his secure communications. In that case only the certificates issued by the trusted authorities are acceptable. See the figure above for a typical example. The API for handling X.509 certificates is described at section sec:x509api. Some examples are listed below.

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5.1.1 X.509 Certificates

An X.509 certificate usually contains information about the certificate holder, the signer, a unique serial number, expiration dates and some other fields [RFC3280] (see section Bibliography) as shown in the table below.


The field that indicates the version of the certificate.


This field holds a unique serial number per certificate.


Holds the issuer's distinguished name.


The activation and expiration dates.


The subject's distinguished name of the certificate.


The extensions are fields only present in version 3 certificates.

The certificate's subject or issuer name is not just a single string. It is a Distinguished name and in the ASN.1 notation is a sequence of several object IDs with their corresponding values. Some of available OIDs to be used in an X.509 distinguished name are defined in `gnutls/x509.h'.

The Version field in a certificate has values either 1 or 3 for version 3 certificates. Version 1 certificates do not support the extensions field so it is not possible to distinguish a CA from a person, thus their usage should be avoided.

The validity dates are there to indicate the date that the specific certificate was activated and the date the certificate's key would be considered invalid.

Certificate extensions are there to include information about the certificate's subject that did not fit in the typical certificate fields. Those may be e-mail addresses, flags that indicate whether the belongs to a CA etc. All the supported X.509 version 3 extensions are shown in the table below.

subject key id (

An identifier of the key of the subject.

authority key id (

An identifier of the authority's key used to sign the certificate.

subject alternative name (

Alternative names to subject's distinguished name.

key usage (

Constraints the key's usage of the certificate.

extended key usage (

Constraints the purpose of the certificate.

basic constraints (

Indicates whether this is a CA certificate or not, and specify the maximum path lengths of certificate chains.

CRL distribution points (

This extension is set by the CA, in order to inform about the issued CRLs.

Proxy Certification Information (

Proxy Certificates includes this extension that contains the OID of the proxy policy language used, and can specify limits on the maximum lengths of proxy chains. Proxy Certificates are specified in [RFC3820] (see section Bibliography).

In GnuTLS the X.509 certificate structures are handled using the gnutls_x509_crt_t type and the corresponding private keys with the gnutls_x509_privkey_t type. All the available functions for X.509 certificate handling have their prototypes in `gnutls/x509.h'. An example program to demonstrate the X.509 parsing capabilities can be found at section ex:x509-info.

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5.1.2 Verifying X.509 Certificate Paths

Verifying certificate paths is important in X.509 authentication. For this purpose the function gnutls_x509_crt_verify is provided. The output of this function is the bitwise OR of the elements of the gnutls_certificate_status_t enumeration. A detailed description of these elements can be found in figure below. The function gnutls_certificate_verify_peers2 is equivalent to the previous one, and will verify the peer's certificate in a TLS session.


The certificate is not signed by one of the known authorities, or the signature is invalid.


The certificate has been revoked by its CA.


The certificate's issuer is not known. This is the case when the issuer is not in the trusted certificates list.


The certificate's signer was not a CA. This may happen if this was a version 1 certificate, which is common with some CAs, or a version 3 certificate without the basic constrains extension.


The certificate was signed using an insecure algorithm such as MD2 or MD5. These algorithms have been broken and should not be trusted.

There is also to possibility to pass some input to the verification functions in the form of flags. For gnutls_x509_crt_verify the flags are passed straightforward, but gnutls_certificate_verify_peers2 depends on the flags set by calling gnutls_certificate_set_verify_flags. All the available flags are part of the enumeration gnutls_certificate_verify_flags and are explained in the table below.


If set a signer does not have to be a certificate authority. This flag should normaly be disabled, unless you know what this means.


Allow only trusted CA certificates that have version 1. This is safer than GNUTLS_VERIFY_ALLOW_ANY_X509_V1_CA_CRT, and should be used instead. That way only signers in your trusted list will be allowed to have certificates of version 1.


Allow CA certificates that have version 1 (both root and intermediate). This is dangerous since those haven't the basicConstraints extension. Must be used in combination with GNUTLS_VERIFY_ALLOW_X509_V1_CA_CRT.


If a certificate is not signed by anyone trusted but exists in the trusted CA list do not treat it as trusted.


Allow certificates to be signed using the old MD2 algorithm.


Allow certificates to be signed using the broken MD5 algorithm.

Although the verification of a certificate path indicates that the certificate is signed by trusted authority, does not reveal anything about the peer's identity. It is required to verify if the certificate's owner is the one you expect. For more information consult [RFC2818] (see section Bibliography) and section ex:verify for an example.

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5.1.3 PKCS #10 Certificate Requests

A certificate request is a structure, which contain information about an applicant of a certificate service. It usually contains a private key, a distinguished name and secondary data such as a challenge password. GnuTLS supports the requests defined in PKCS #10 [RFC2986] (see section Bibliography). Other certificate request's format such as PKIX's [RFC4211] (see section Bibliography) are not currently supported.

In GnuTLS the PKCS #10 structures are handled using the gnutls_x509_crq_t type. An example of a certificate request generation can be found at section ex:crq.

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5.1.4 PKCS #12 Structures

A PKCS #12 structure [PKCS12] (see section Bibliography) usually contains a user's private keys and certificates. It is commonly used in browsers to export and import the user's identities.

In GnuTLS the PKCS #12 structures are handled using the gnutls_pkcs12_t type. This is an abstract type that may hold several gnutls_pkcs12_bag_t types. The Bag types are the holders of the actual data, which may be certificates, private keys or encrypted data. An Bag of type encrypted should be decrypted in order for its data to be accessed.

An example of a PKCS #12 structure generation can be found at section ex:pkcs12.

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5.2 The OpenPGP Trust Model

The OpenPGP key authentication relies on a distributed trust model, called the "web of trust". The "web of trust" uses a decentralized system of trusted introducers, which are the same as a CA. OpenPGP allows anyone to sign anyone's else public key. When Alice signs Bob's key, she is introducing Bob's key to anyone who trusts Alice. If someone trusts Alice to introduce keys, then Alice is a trusted introducer in the mind of that observer.


For example: If David trusts Alice to be an introducer, and Alice signed Bob's key, Dave also trusts Bob's key to be the real one.

There are some key points that are important in that model. In the example Alice has to sign Bob's key, only if she is sure that the key belongs to Bob. Otherwise she may also make Dave falsely believe that this is Bob's key. Dave has also the responsibility to know who to trust. This model is similar to real life relations.

Just see how Charlie behaves in the previous example. Although he has signed Bob's key - because he knows, somehow, that it belongs to Bob - he does not trust Bob to be an introducer. Charlie decided to trust only Kevin, for some reason. A reason could be that Bob is lazy enough, and signs other people's keys without being sure that they belong to the actual owner.

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5.2.1 OpenPGP Keys

In GnuTLS the OpenPGP key structures [RFC2440] (see section Bibliography) are handled using the gnutls_openpgp_crt_t type and the corresponding private keys with the gnutls_openpgp_privkey_t type. All the prototypes for the key handling functions can be found at `gnutls/openpgp.h'.

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5.2.2 Verifying an OpenPGP Key

The verification functions of OpenPGP keys, included in GnuTLS, are simple ones, and do not use the features of the "web of trust". For that reason, if the verification needs are complex, the assistance of external tools like GnuPG and GPGME (http://www.gnupg.org/related_software/gpga>) is recommended.

There is one verification function in GnuTLS, the gnutls_openpgp_crt_verify_ring. This checks an OpenPGP key against a given set of public keys (keyring) and returns the key status. The key verification status is the same as in X.509 certificates, although the meaning and interpretation are different. For example an OpenPGP key may be valid, if the self signature is ok, even if no signers were found. The meaning of verification status is shown in the figure below.


A signature on the key is invalid. That means that the key was modified by somebody, or corrupted during transport.


The key has been revoked by its owner.


The key was not signed by a known signer.


The certificate was signed using an insecure algorithm such as MD2 or MD5. These algorithms have been broken and should not be trusted.

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5.3 Digital Signatures

In this section we will provide some information about digital signatures, how they work, and give the rationale for disabling some of the algorithms used.

Digital signatures work by using somebody's secret key to sign some arbitrary data. Then anybody else could use the public key of that person to verify the signature. Since the data may be arbitrary it is not suitable input to a cryptographic digital signature algorithm. For this reason and also for performance cryptographic hash algorithms are used to preprocess the input to the signature algorithm. This works as long as it is difficult enough to generate two different messages with the same hash algorithm output. In that case the same signature could be used as a proof for both messages. Nobody wants to sign an innocent message of donating 1 € to Greenpeace and find out that he donated 1.000.000 € to Bad Inc.

For a hash algorithm to be called cryptographic the following three requirements must hold:

  1. Preimage resistance. That means the algorithm must be one way and given the output of the hash function H(x), it is impossible to calculate x.
  2. 2nd preimage resistance. That means that given a pair x,y with y=H(x) it is impossible to calculate an x' such that y=H(x').
  3. Collision resistance. That means that it is impossible to calculate random x and x' such H(x')=H(x).

The last two requirements in the list are the most important in digital signatures. These protect against somebody who would like to generate two messages with the same hash output. When an algorithm is considered broken usually it means that the Collision resistance of the algorithm is less than brute force. Using the birthday paradox the brute force attack takes 2^{((hash size) / 2) operations. Today colliding certificates using the MD5 hash algorithm have been generated as shown in [WEGER] (see section Bibliography).

There has been cryptographic results for the SHA-1 hash algorithms as well, although they are not yet critical. Before 2004, MD5 had a presumed collision strength of 2^{64, but it has been showed to have a collision strength well under 2^{50. As of November 2005, it is believed that SHA-1's collision strength is around 2^{63. We consider this sufficiently hard so that we still support SHA-1. We anticipate that SHA-256/386/512 will be used in publicly-distributed certificates in the future. When 2^{63 can be considered too weak compared to the computer power available sometime in the future, SHA-1 will be disabled as well. The collision attacks on SHA-1 may also get better, given the new interest in tools for creating them.

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5.3.1 Trading Security for Interoperability

If you connect to a server and use GnuTLS' functions to verify the certificate chain, and get a GNUTLS_CERT_INSECURE_ALGORITHM validation error (see section Verifying X.509 Certificate Paths), it means that somewhere in the certificate chain there is a certificate signed using RSA-MD2 or RSA-MD5. These two digital signature algorithms are considered broken, so GnuTLS fail when attempting to verify the certificate. In some situations, it may be useful to be able to verify the certificate chain anyway, assuming an attacker did not utilize the fact that these signatures algorithms are broken. This section will give help on how to achieve that.

First, it is important to know that you do not have to enable any of the flags discussed here to be able to use trusted root CA certificates signed using RSA-MD2 or RSA-MD5. The only attack today is that it is possible to generate certificates with colliding signatures (collision resistance); you cannot generate a certificate that has the same signature as an already existing signature (2nd preimage resistance).

If you are using gnutls_certificate_verify_peers2 to verify the certificate chain, you can call gnutls_certificate_set_verify_flags with the GNUTLS_VERIFY_ALLOW_SIGN_RSA_MD2 or GNUTLS_VERIFY_ALLOW_SIGN_RSA_MD5 flag, as in:

  gnutls_certificate_set_verify_flags (x509cred,

This will tell the verifier algorithm to enable RSA-MD5 when verifying the certificates.

If you are using gnutls_x509_crt_verify or gnutls_x509_crt_list_verify, you can pass the GNUTLS_VERIFY_ALLOW_SIGN_RSA_MD5 parameter directly in the flags parameter.

If you are using these flags, it may also be a good idea to warn the user when verification failure occur for this reason. The simplest is to not use the flags by default, and only fall back to using them after warning the user. If you wish to inspect the certificate chain yourself, you can use gnutls_certificate_get_peers to extract the raw server's certificate chain, then use gnutls_x509_crt_import to parse each of the certificates, and then use gnutls_x509_crt_get_signature_algorithm to find out the signing algorithm used for each certificate. If any of the intermediary certificates are using GNUTLS_SIGN_RSA_MD2 or GNUTLS_SIGN_RSA_MD5, you could present a warning.

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