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In cryptography, X.509 is a standard that defines the format of public key certificates. X.509 certificates are used in many Internet protocols, including TLS/SSL, which is the basis for HTTPS, the secure protocol for browsing the web. They are also used in offline applications, like electronic signatures. An X.509 certificate contains a public key and an identity (a hostname, or an organization, or an individual), and is either signed by a certificate authority or self-signed. When a certificate is signed by a trusted certificate authority, or validated by other means, someone holding that certificate can rely on the public key it contains to establish secure communications with another party, or validate documents digitally signed by the corresponding private key.
Besides the format for certificates themselves, X.509 specifies certificate revocation lists as a means to distribute information about certificates that are no longer valid, and a certification path validation algorithm, which allows for certificates to be signed by intermediate CA certificates, which are in turn signed by other certificates, eventually reaching a trust anchor.
X.509 was initially issued on July 3, 1988 and was begun in association with the X.500 standard. It assumes a strict hierarchical system of certificate authorities (CAs) for issuing the certificates. This contrasts with web of trust models, like PGP, where anyone (not just special CAs) may sign and thus attest to the validity of others' key certificates. Version 3 of X.509 includes the flexibility to support other topologies like bridges and meshes. It can be used in a peer-to-peer, OpenPGP-like web of trust, but was rarely used that way as of 2004. The X.500 system has only been implemented by sovereign nations for state identity information sharing treaty fulfillment purposes, and the IETF's Public-Key Infrastructure (X.509), or PKIX, working group has adapted the standard to the more flexible organization of the Internet. In fact, the term X.509 certificate usually refers to the IETF's PKIX certificate and CRL Profile of the X.509 v3 certificate standard, as specified in RFC 5280, commonly called PKIX for Public Key Infrastructure (X.509).
In the X.509 system, an organization that wants a signed certificate requests one via a certificate signing request (CSR).
To do this, it first generates a key pair, keeping the private key secret and using it to sign the CSR. This contains information identifying the applicant and the applicant's public key that is used to verify the signature of the CSR - and the Distinguished Name (DN) that the certificate is for. The CSR may be accompanied by other credentials or proofs of identity required by the certificate authority.
An organization's trusted root certificates can be distributed to all employees so that they can use the company PKI system. Browsers such as Internet Explorer, Firefox, Opera, Safari and Chrome come with a predetermined set of root certificates pre-installed, so SSL certificates from major certificate authorities will work instantly; in effect the browsers' developers determine which CAs are trusted third parties for the browsers' users. For example, Firefox provides a CSV and/or HTML file containing a list of Included CAs.
X.509 also includes standards for certificate revocation list (CRL) implementations, an often neglected aspect of PKI systems. The IETF-approved way of checking a certificate's validity is the Online Certificate Status Protocol (OCSP). Firefox 3 enables OCSP checking by default, as do versions of Windows from at least Vista and later.
The structure foreseen by the standards is expressed in a formal language, Abstract Syntax Notation One (ASN.1).
The structure of an X.509 v3 digital certificate is as follows:
Each extension has its own ID, expressed as object identifier, which is a set of values, together with either a critical or non-critical indication. A certificate-using system must reject the certificate if it encounters a critical extension that it does not recognize, or a critical extension that contains information that it cannot process. A non-critical extension may be ignored if it is not recognized, but must be processed if it is recognized.
The structure of version 1 is given in RFC 1422.
ITU-T introduced issuer and subject unique identifiers in version 2 to permit the reuse of issuer or subject name after some time. An example of reuse will be when a CA goes bankrupt and its name is deleted from the country's public list. After some time another CA with the same name may register itself, even though it is unrelated to the first one. However, IETF recommends that no issuer and subject names be reused. Therefore, version 2 is not widely deployed in the Internet.
Extensions were introduced in version 3. A CA can use extensions to issue a certificate only for a specific purpose (e.g. only for signing digital objects).
In all versions, the serial number must be unique for each certificate issued by a specific CA (as mentioned in RFC 2459).
RFC 5280 (and its predecessors) defines a number of certificate extensions which indicate how the certificate should be used. Most of them are arcs from the joint-iso-ccitt(2) ds(5) id-ce(29) OID. Some of the most common, defined in section 4.2.1, are:
In general, if a certificate has several extensions restricting its use, all restrictions must be satisfied for a given use to be appropriate. RFC 5280 gives the specific example of a certificate containing both keyUsage and extendedKeyUsage: in this case, both must be processed and the certificate can only be used if both extensions are coherent in specifying the usage of a certificate. For example, NSS uses both extensions to specify certificate usage.
There are several commonly used filename extensions for X.509 certificates. Unfortunately, some of these extensions are also used for other data such as private keys.
PKCS#7 is a standard for signing or encrypting (officially called "enveloping") data. Since the certificate is needed to verify signed data, it is possible to include them in the SignedData structure. A .P7C file is a degenerated SignedData structure, without any data to sign.
A certificate chain (see the equivalent concept of "certification path" defined by RFC 5280) is a list of certificates (usually starting with an end-entity certificate) followed by one or more CA certificates (usually the last one being a self-signed certificate), with the following properties:
Certificate chains are used in order to check that the public key (PK) contained in a target certificate (the first certificate in the chain) and other data contained in it effectively belongs to its subject. In order to ascertain this, the signature on the target certificate is verified by using the PK contained in the following certificate, whose signature is verified using the next certificate, and so on until the last certificate in the chain is reached. As the last certificate is a trust anchor, successfully reaching it will prove that the target certificate can be trusted.
The description in the preceding paragraph is a simplified view on the certification path validation process as defined by RFC 5280, which involves additional checks, such as verifying validity dates on certificates, looking up CRLs, etc.
Examining how certificate chains are built and validated, it is important to note that a concrete certificate can be part of very different certificate chains (all of them valid). This is because several CA certificates can be generated for the same subject and public key, but be signed with different private keys (from different CAs or different private keys from the same CA). So, although a single X.509 certificate can have only one issuer and one CA signature, it can be validly linked to more than one certificate, building completely different certificate chains. This is crucial for cross-certification between PKIs and other applications.  See the following examples.
In these diagrams:
In order to manage that user certificates existing in PKI 2 (like "User 2") are trusted by PKI 1, CA1 generates a certificate (cert2.1) containing the public key of CA2.  Now both "cert2 and cert2.1 (in green) have the same subject and public key, so there are two valid chains for cert2.2 (User 2): "cert2.2 → cert2" and "cert2.2 → cert2.1 → cert1".
Similarly, CA2 can generate a certificate (cert1.1) containing the public key of CA1 so that user certificates existing in PKI 1 (like "User 1") are trusted by PKI 2.
Understanding Certification Path Construction (PDF). PKI Forum. September 2002.
To allow for graceful transition from the old signing key pair to the new signing key pair, the CA should issue a certificate that contains the old public key signed by the new private signing key and a certificate that contains the new public key signed by the old private signing key. Both of these certificates are self-issued, but neither is self-signed. Note that these are in addition to the two self-signed certificates (one old, one new).
Since both cert1 and cert3 contain the same public key (the old one), there are two valid certificate chains for cert5: "cert5 → cert1" and "cert5 → cert3 → cert2", and analogously for cert6. This allows that old user certificates (such as cert5) and new certificates (such as cert6) can be trusted indifferently by a party having either the new root CA certificate or the old one as trust anchor during the transition to the new CA keys.
This is an example of a decoded X.509 certificate for wikipedia.org and several other Wikipedia websites. It was issued by GlobalSign, as stated in the Issuer field. Its Subject field describes Wikipedia as an organization, and its Subject Alternative Name field describes the hostnames for which it can be used. The Subject Public Key Info field contains an ECDSA public key, while the signature at the bottom is generated by GlobalSign's RSA private key.
Certificate: Data: Version: 3 (0x2) Serial Number: 10:e6:fc:62:b7:41:8a:d5:00:5e:45:b6 Signature Algorithm: sha256WithRSAEncryption Issuer: C=BE, O=GlobalSign nv-sa, CN=GlobalSign Organization Validation CA - SHA256 - G2 Validity Not Before: Nov 21 08:00:00 2016 GMT Not After : Nov 22 07:59:59 2017 GMT Subject: C=US, ST=California, L=San Francisco, O=Wikimedia Foundation, Inc., CN=*.wikipedia.org Subject Public Key Info: Public Key Algorithm: id-ecPublicKey Public-Key: (256 bit) pub: 04:c9:22:69:31:8a:d6:6c:ea:da:c3:7f:2c:ac:a5: af:c0:02:ea:81:cb:65:b9:fd:0c:6d:46:5b:c9:1e: ed:b2:ac:2a:1b:4a:ec:80:7b:e7:1a:51:e0:df:f7: c7:4a:20:7b:91:4b:20:07:21:ce:cf:68:65:8c:c6: 9d:3b:ef:d5:c1 ASN1 OID: prime256v1 NIST CURVE: P-256 X509v3 extensions: X509v3 Key Usage: critical Digital Signature, Key Agreement Authority Information Access: CA Issuers - URI:http://secure.globalsign.com/cacert/gsorganizationvalsha2g2r1.crt OCSP - URI:http://ocsp2.globalsign.com/gsorganizationvalsha2g2 X509v3 Certificate Policies: Policy: 22.214.171.124.4.1.4146.1.20 CPS: https://www.globalsign.com/repository/ Policy: 126.96.36.199.2.2 X509v3 Basic Constraints: CA:FALSE X509v3 CRL Distribution Points: Full Name: URI:http://crl.globalsign.com/gs/gsorganizationvalsha2g2.crl X509v3 Subject Alternative Name: DNS:*.wikipedia.org, DNS:*.m.mediawiki.org, DNS:*.m.wikibooks.org, DNS:*.m.wikidata.org, DNS:*.m.wikimedia.org, DNS:*.m.wikimediafoundation.org, DNS:*.m.wikinews.org, DNS:*.m.wikipedia.org, DNS:*.m.wikiquote.org, DNS:*.m.wikisource.org, DNS:*.m.wikiversity.org, DNS:*.m.wikivoyage.org, DNS:*.m.wiktionary.org, DNS:*.mediawiki.org, DNS:*.planet.wikimedia.org, DNS:*.wikibooks.org, DNS:*.wikidata.org, DNS:*.wikimedia.org, DNS:*.wikimediafoundation.org, DNS:*.wikinews.org, DNS:*.wikiquote.org, DNS:*.wikisource.org, DNS:*.wikiversity.org, DNS:*.wikivoyage.org, DNS:*.wiktionary.org, DNS:*.wmfusercontent.org, DNS:*.zero.wikipedia.org, DNS:mediawiki.org, DNS:w.wiki, DNS:wikibooks.org, DNS:wikidata.org, DNS:wikimedia.org, DNS:wikimediafoundation.org, DNS:wikinews.org, DNS:wikiquote.org, DNS:wikisource.org, DNS:wikiversity.org, DNS:wikivoyage.org, DNS:wiktionary.org, DNS:wmfusercontent.org, DNS:wikipedia.org X509v3 Extended Key Usage: TLS Web Server Authentication, TLS Web Client Authentication X509v3 Subject Key Identifier: 28:2A:26:2A:57:8B:3B:CE:B4:D6:AB:54:EF:D7:38:21:2C:49:5C:36 X509v3 Authority Key Identifier: keyid:96:DE:61:F1:BD:1C:16:29:53:1C:C0:CC:7D:3B:83:00:40:E6:1A:7C Signature Algorithm: sha256WithRSAEncryption 8b:c3:ed:d1:9d:39:6f:af:40:72:bd:1e:18:5e:30:54:23:35: ...
To validate this end-entity certificate, one needs an intermediate certificate that matches its Issuer and Authority Key Identifier:
|Issuer||C=BE, O=GlobalSign nv-sa, CN=GlobalSign Organization Validation CA - SHA256 - G2|
|Authority Key Identifier||96:DE:61:F1:BD:1C:16:29:53:1C:C0:CC:7D:3B:83:00:40:E6:1A:7C|
In a TLS connection, a properly-configured server would provide the intermediate as part of the handshake. However, it's also possible to retrieve the intermediate certificate by fetching the "CA Issuers" URL from the end-entity certificate.
This is an example of an intermediate certificate belonging to a certificate authority. This certificate signed the end-entity certificate above, and was signed by the root certificate below. Note that the subject field of this intermediate certificate matches the issuer field of the end-entity certificate that it signed. Also, the "subject key identifier" field in the intermediate matches the "authority key identifier" field in the end-entity certificate.
Certificate: Data: Version: 3 (0x2) Serial Number: 04:00:00:00:00:01:44:4e:f0:42:47 Signature Algorithm: sha256WithRSAEncryption Issuer: C=BE, O=GlobalSign nv-sa, OU=Root CA, CN=GlobalSign Root CA Validity Not Before: Feb 20 10:00:00 2014 GMT Not After : Feb 20 10:00:00 2024 GMT Subject: C=BE, O=GlobalSign nv-sa, CN=GlobalSign Organization Validation CA - SHA256 - G2 Subject Public Key Info: Public Key Algorithm: rsaEncryption Public-Key: (2048 bit) Modulus: 00:c7:0e:6c:3f:23:93:7f:cc:70:a5:9d:20:c3:0e: ... Exponent: 65537 (0x10001) X509v3 extensions: X509v3 Key Usage: critical Certificate Sign, CRL Sign X509v3 Basic Constraints: critical CA:TRUE, pathlen:0 X509v3 Subject Key Identifier: 96:DE:61:F1:BD:1C:16:29:53:1C:C0:CC:7D:3B:83:00:40:E6:1A:7C X509v3 Certificate Policies: Policy: X509v3 Any Policy CPS: https://www.globalsign.com/repository/ X509v3 CRL Distribution Points: Full Name: URI:http://crl.globalsign.net/root.crl Authority Information Access: OCSP - URI:http://ocsp.globalsign.com/rootr1 X509v3 Authority Key Identifier: keyid:60:7B:66:1A:45:0D:97:CA:89:50:2F:7D:04:CD:34:A8:FF:FC:FD:4B Signature Algorithm: sha256WithRSAEncryption 46:2a:ee:5e:bd:ae:01:60:37:31:11:86:71:74:b6:46:49:c8: ...
This is an example of a self-signed root certificate representing a certificate authority. Its issuer and subject fields are the same, and its signature can be validated with its own public key. Validation of the trust chain has to end here. If the validating program has this root certificate in its trust store, the end-entity certificate can be considered trusted for use in a TLS connection. Otherwise, the end-entity certificate is considered untrusted.
Certificate: Data: Version: 3 (0x2) Serial Number: 04:00:00:00:00:01:15:4b:5a:c3:94 Signature Algorithm: sha1WithRSAEncryption Issuer: C=BE, O=GlobalSign nv-sa, OU=Root CA, CN=GlobalSign Root CA Validity Not Before: Sep 1 12:00:00 1998 GMT Not After : Jan 28 12:00:00 2028 GMT Subject: C=BE, O=GlobalSign nv-sa, OU=Root CA, CN=GlobalSign Root CA Subject Public Key Info: Public Key Algorithm: rsaEncryption Public-Key: (2048 bit) Modulus: 00:da:0e:e6:99:8d:ce:a3:e3:4f:8a:7e:fb:f1:8b: ... Exponent: 65537 (0x10001) X509v3 extensions: X509v3 Key Usage: critical Certificate Sign, CRL Sign X509v3 Basic Constraints: critical CA:TRUE X509v3 Subject Key Identifier: 60:7B:66:1A:45:0D:97:CA:89:50:2F:7D:04:CD:34:A8:FF:FC:FD:4B Signature Algorithm: sha1WithRSAEncryption d6:73:e7:7c:4f:76:d0:8d:bf:ec:ba:a2:be:34:c5:28:32:b5: ...
Implementations suffer from design flaws, bugs, different interpretations of standards and lack of interoperability of different standards. Some problems are:
Digital signature systems depend on secure cryptographic hash functions to work. When a public key infrastructure allows the use of a hash function that is no longer secure, an attacker can exploit weaknesses in the hash function to forge certificates. Specifically, if an attacker is able to produce a hash collision, they can convince a CA to sign a certificate with innocuous contents, where the hash of those contents is identical to the hash of another, malicious set of certificate contents, created by the attacker with values of their choosing. The attacker can then append the CA-provided signature to their malicious certificate contents, resulting in a malicious certificate that appears to be signed by the CA. Because the malicious certificate contents are chosen solely by the attacker, they can have different validity dates or hostnames than the innocuous certificate. The malicious certificate can even contain a "CA: true" field making it able to issue further trusted certificates.
Exploiting a hash collision to forge X.509 signatures requires that the attacker be able to predict the data that the certificate authority will sign. This can be somewhat mitigated by the CA generating a random component in the certificates it signs, typically the serial number. The CA/Browser Forum has required serial number entropy in its Baseline Requirements Section 7.1 since 2011.
As of January 1, 2016[update], the Baseline Requirements forbid issuance of certificates using SHA-1. As of early 2017[update], Chrome and Firefox reject certificates that use SHA-1. As of May 2017[update] both Edge and Safari  are also rejecting SHA-1 certificate. Non-browser X.509 validators do not yet reject SHA-1 certificates.
In 1995, the Internet Engineering Task Force in conjunction with the National Institute of Standards and Technology formed the Public-Key Infrastructure (X.509) working group. The working group, concluded in June 2014, is commonly referred to as "PKIX." It produced RFCs and other standards documentation on using deploying X.509 in practice. In particular it produced RFC 3280 and its successor RFC 5280, which define how to use X.509 in Internet protocols.
TLS/SSL and HTTPS use the RFC 5280 profile of X.509, as do S/MIME (Secure Multipurpose Internet Mail Extensions) and the EAP-TLS method for WiFi authentication. Any protocol that uses TLS, such as SMTP, POP, IMAP, LDAP, XMPP, and many more, inherently uses X.509. IPsec uses its own profile of X.509, defined in RFC 4945.
The OpenCable security specification defines its own profile of X.509 for use in the cable industry.
The Microsoft Authenticode code signing system uses X.509 to identify authors of computer programs.
The OPC UA industrial automation communication standard uses X.509.
SSH generally uses a Trust On First Use security model and doesn't have need for certificates. However, the popular OpenSSH implementation does support a CA-signed identity model based on its own non-X.509 certificate format.