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diff --git a/doc/user/project/repository/x509_signed_commits/index.md b/doc/user/project/repository/x509_signed_commits/index.md
index 7c115734345..17031dd29af 100644
--- a/doc/user/project/repository/x509_signed_commits/index.md
+++ b/doc/user/project/repository/x509_signed_commits/index.md
@@ -5,72 +5,82 @@ info: "To determine the technical writer assigned to the Stage/Group associated
type: concepts, howto
---
-# Signing commits and tags with X.509 **(FREE)**
+# Sign commits and tags with X.509 certificates **(FREE)**
> [Introduced](https://gitlab.com/gitlab-org/gitlab/-/merge_requests/17773) in GitLab 12.8.
[X.509](https://en.wikipedia.org/wiki/X.509) is a standard format for public key
certificates issued by a public or private Public Key Infrastructure (PKI).
Personal X.509 certificates are used for authentication or signing purposes
-such as SMIME, but Git also supports signing of commits and tags
-with X.509 certificates in a similar way as with [GPG](../gpg_signed_commits/index.md).
-The main difference is the trust anchor which is the PKI for X.509 certificates
-instead of a web of trust with GPG.
-
-## How GitLab handles X.509
-
-GitLab uses its own certificate store and therefore defines the trust chain.
-
+such as S/MIME (Secure/Multipurpose Internet Mail Extensions).
+However, Git also supports signing of commits and tags with X.509 certificates in a
+similar way as with [GPG (GnuPG, or GNU Privacy Guard)](../gpg_signed_commits/index.md).
+The main difference is the way GitLab determines whether or not the developer's signature is trusted:
+
+- For X.509, a root certificate authority is added to the GitLab trust store.
+ (A trust store is a repository of trusted security certificates.) Combined with
+ any required intermediate certificates in the signature, the developer's certificate
+ can be chained back to a trusted root certificate.
+- For GPG, developers [add their GPG key](../gpg_signed_commits/index.md#adding-a-gpg-key-to-your-account)
+ to their account.
+
+GitLab uses its own certificate store and therefore defines the
+[trust chain](https://www.ssl.com/faqs/what-is-a-chain-of-trust/).
For a commit or tag to be *verified* by GitLab:
-- The signing certificate email must match a verified email address used by the committer in GitLab.
-- The Certificate Authority has to be trusted by the GitLab instance, see also
- [Omnibus install custom public certificates](https://docs.gitlab.com/omnibus/settings/ssl.html#install-custom-public-certificates).
-- The signing time has to be within the time range of the [certificate validity](https://www.rfc-editor.org/rfc/rfc5280.html#section-4.1.2.5)
+- The signing certificate email must match a verified email address in GitLab.
+- The GitLab instance must be able to establish a full [trust chain](https://www.ssl.com/faqs/what-is-a-chain-of-trust/)
+ from the certificate in the signature to a trusted certificate in the GitLab certificate store.
+ This chain may include intermediate certificates supplied in the signature. You may
+ need to add certificates, such as Certificate Authority root certificates,
+ [to the GitLab certificate store](https://docs.gitlab.com/omnibus/settings/ssl.html#install-custom-public-certificates).
+- The signing time must be in the time range of the
+ [certificate validity](https://www.rfc-editor.org/rfc/rfc5280.html#section-4.1.2.5),
which is usually up to three years.
-- The signing time is equal or later than commit time.
-
-NOTE:
-Certificate revocation lists are checked on a daily basis via background worker.
+- The signing time is equal to, or later than, the commit time.
-NOTE:
-Self signed certificates without `authorityKeyIdentifier`,
-`subjectKeyIdentifier`, and `crlDistributionPoints` are not supported. We
-recommend using certificates from a PKI that are in line with
-[RFC 5280](https://tools.ietf.org/html/rfc5280).
+If a commit's status has already been determined and stored in the database,
+use the Rake task [to re-check the status](../../../../raketasks/x509_signatures.md).
+Refer to the [Troubleshooting section](#troubleshooting).
+GitLab checks certificate revocation lists on a daily basis with a background worker.
## Limitations
+- Self-signed certificates without `authorityKeyIdentifier`,
+ `subjectKeyIdentifier`, and `crlDistributionPoints` are not supported. We
+ recommend using certificates from a PKI that are in line with
+ [RFC 5280](https://tools.ietf.org/html/rfc5280).
- If you have more than one email in the Subject Alternative Name list in
your signing certificate,
[only the first one is used to verify commits](https://gitlab.com/gitlab-org/gitlab/-/issues/336677).
- The `X509v3 Subject Key Identifier` (SKI) in the issuer certificate and the
signing certificate
[must be 40 characters long](https://gitlab.com/gitlab-org/gitlab/-/issues/332503).
- If your SKI is shorter, commits will not show as verified in GitLab, and
+ If your SKI is shorter, commits don't show as verified in GitLab, and
short subject key identifiers may also
[cause errors when accessing the project](https://gitlab.com/gitlab-org/gitlab/-/issues/332464),
such as 'An error occurred while loading commit signatures' and
`HTTP 422 Unprocessable Entity` errors.
-## Obtaining an X.509 key pair
+## Configure for signed commits
-If your organization has Public Key Infrastructure (PKI), that PKI provides
-an S/MIME key.
+To sign your commits, tags, or both, you must:
-If you do not have an S/MIME key pair from a PKI, you can either create your
-own self-signed one, or purchase one. MozillaZine keeps a nice collection
-of [S/MIME-capable signing authorities](http://kb.mozillazine.org/Getting_an_SMIME_certificate)
-and some of them generate keys for free.
+1. [Obtain an X.509 key pair](#obtain-an-x509-key-pair).
+1. [Associate your X.509 certificate with Git](#associate-your-x509-certificate-with-git).
+1. [Sign and verify commits](#sign-and-verify-commits).
+1. [Sign and verify tags](#sign-and-verify-tags).
-## Associating your X.509 certificate with Git
+### Obtain an X.509 key pair
-To take advantage of X.509 signing, you need Git 2.19.0 or later. You can
-check your Git version with:
+If your organization has Public Key Infrastructure (PKI), that PKI provides
+an S/MIME key. If you do not have an S/MIME key pair from a PKI, you can either
+create your own self-signed pair, or purchase a pair.
-```shell
-git --version
-```
+### Associate your X.509 certificate with Git
+
+To take advantage of X.509 signing, you need Git 2.19.0 or later. You can
+check your Git version with the command `git --version`.
If you have the correct version, you can proceed to configure Git.
@@ -84,71 +94,267 @@ git config --global user.signingkey $signingkey
git config --global gpg.format x509
```
-### Windows and MacOS
+#### Windows and macOS
-Install [S/MIME Sign](https://github.com/github/smimesign) by downloading the
-installer or via `brew install smimesign` on MacOS.
+To configure Windows or macOS:
-Get the ID of your certificate with `smimesign --list-keys` and set your
-signing key `git config --global user.signingkey ID`, then configure X.509:
+1. Install [S/MIME Sign](https://github.com/github/smimesign) by either:
+ - Downloading the installer.
+ - Running `brew install smimesign` on macOS.
+1. Get the ID of your certificate by running `smimesign --list-keys`.
+1. Set your signing key by running `git config --global user.signingkey ID`.
+1. Configure X.509 with this command:
-```shell
-git config --global gpg.x509.program smimesign
-git config --global gpg.format x509
-```
+ ```shell
+ git config --global gpg.x509.program smimesign
+ git config --global gpg.format x509
+ ```
-## Signing commits
+### Sign and verify commits
-After you have [associated your X.509 certificate with Git](#associating-your-x509-certificate-with-git) you
-can start signing your commits:
+After you have [associated your X.509 certificate with Git](#associate-your-x509-certificate-with-git) you
+can sign your commits:
-1. Commit like you used to, the only difference is the addition of the `-S` flag:
+1. When you create a Git commit, add the `-S` flag:
```shell
git commit -S -m "feat: x509 signed commits"
```
-1. Push to GitLab and check that your commits [are verified](#verifying-commits).
+1. Push to GitLab, and check that your commits are verified with the `--show-signature` flag:
-If you don't want to type the `-S` flag every time you commit, you can tell Git
-to sign your commits automatically:
-
-```shell
-git config --global commit.gpgsign true
-```
-
-## Verifying commits
+ ```shell
+ git log --show-signature
+ ```
-To verify that a commit is signed, you can use the `--show-signature` flag:
+1. *If you don't want to type the `-S` flag every time you commit,* run this command
+ for Git to sign your commits every time:
-```shell
-git log --show-signature
-```
+ ```shell
+ git config --global commit.gpgsign true
+ ```
-## Signing tags
+### Sign and verify tags
-After you have [associated your X.509 certificate with Git](#associating-your-x509-certificate-with-git) you
+After you have [associated your X.509 certificate with Git](#associate-your-x509-certificate-with-git) you
can start signing your tags:
-1. Tag like you used to, the only difference is the addition of the `-s` flag:
+1. When you create a Git tag, add the `-s` flag:
```shell
git tag -s v1.1.1 -m "My signed tag"
```
-1. Push to GitLab and check that your tags [are verified](#verifying-tags).
+1. Push to GitLab and verify your tags are signed with this command:
+
+ ```shell
+ git tag --verify v1.1.1
+ ```
+
+1. *If you don't want to type the `-s` flag every time you tag,* run this command
+ for Git to sign your tags each time:
-If you don't want to type the `-s` flag every time you tag, you can tell Git
-to sign your tags automatically:
+ ```shell
+ git config --global tag.gpgsign true
+ ```
-```shell
-git config --global tag.gpgsign true
-```
+## Resources
-## Verifying tags
+- [Rake task for X.509 signatures](../../../../raketasks/x509_signatures.md)
-To verify that a tag is signed, you can use the `--verify` flag:
+## Troubleshooting
+
+### Re-verify commits
+
+GitLab stores the status of any checked commits in the database. You can use a
+Rake task to [check the status of any previously checked commits](../../../../raketasks/x509_signatures.md).
+
+After you make any changes, run this command:
```shell
-git tag --verify v1.1.1
+sudo gitlab-rake gitlab:x509:update_signatures
```
+
+### Main verification checks
+
+The code performs
+[these key checks](https://gitlab.com/gitlab-org/gitlab/-/blob/v14.1.0-ee/lib/gitlab/x509/signature.rb#L33),
+which all must return `verified`:
+
+- `x509_certificate.nil?` should be false.
+- `x509_certificate.revoked?` should be false.
+- `verified_signature` should be true.
+- `user.nil?` should be false.
+- `user.verified_emails.include?(@email)` should be true.
+- `certificate_email == @email` should be true.
+
+To investigate why a commit shows as `Unverified`:
+
+1. [Start a Rails console](../../../../administration/operations/rails_console.md#starting-a-rails-console-session):
+
+ ```shell
+ sudo gitlab-rails console
+ ```
+
+1. Identify the project (either by path or ID) and full commit SHA that you're investigating.
+ Use this information to create `signature` to run other checks against:
+
+ ```ruby
+ project = Project.find_by_full_path('group/subgroup/project')
+ project = Project.find_by_id('121')
+ commit = project.repository.commit_by(oid: '87fdbd0f9382781442053b0b76da729344e37653')
+ signedcommit=Gitlab::X509::Commit.new(commit)
+ signature=Gitlab::X509::Signature.new(signedcommit.signature_text, signedcommit.signed_text, commit.committer_email, commit.created_at)
+ ```
+
+ If you make changes to address issues identified running through the checks, restart the
+ Rails console and run though the checks again from the start.
+
+1. Check the certificate on the commit:
+
+ ```ruby
+ signature.x509_certificate.nil?
+ signature.x509_certificate.revoked?
+ ```
+
+ Both checks should return `false`:
+
+ ```ruby
+ > signature.x509_certificate.nil?
+ => false
+ > signature.x509_certificate.revoked?
+ => false
+ ```
+
+ A [known issue](https://gitlab.com/gitlab-org/gitlab/-/issues/332503) causes
+ these checks to fail with `Validation failed: Subject key identifier is invalid`.
+
+1. Run a cryptographic check on the signature. The code must return `true`:
+
+ ```ruby
+ signature.verified_signature
+ ```
+
+ If it returns `false` then [investigate this check further](#cryptographic-verification-checks).
+
+1. Confirm the email addresses match on the commit and the signature:
+
+ - The Rails console displays the email addresses being compared.
+ - The final command must return `true`:
+
+ ```ruby
+ sigemail=signature.__send__:certificate_email
+ commitemail=commit.committer_email
+ sigemail == commitemail
+ ```
+
+ A [known issue](https://gitlab.com/gitlab-org/gitlab/-/issues/336677) exists:
+ only the first email in the `Subject Alternative Name` list is compared. To
+ display the `Subject Alternative Name` list, run:
+
+ ```ruby
+ signature.__send__ :get_certificate_extension,'subjectAltName'
+ ```
+
+ If the developer's email address is not the first one in the list, this check
+ fails, and the commit is marked `unverified`.
+
+1. The email address on the commit must be associated with an account in GitLab.
+ This check should return `false`:
+
+ ```ruby
+ signature.user.nil?
+ ```
+
+1. Check the email address is associated with a user in GitLab. This check should
+ return a user, such as `#<User id:1234 @user_handle>`:
+
+ ```ruby
+ User.find_by_any_email(commit.committer_email)
+ ```
+
+ If it returns `nil`, the email address is not associated with a user, and the check fails.
+
+1. Confirm the developer's email address is verified. This check must return true:
+
+ ```ruby
+ signature.user.verified_emails.include?(commit.committer_email)
+ ```
+
+ If the previous check returned `nil`, this command displays an error:
+
+ ```plaintext
+ NoMethodError (undefined method `verified_emails' for nil:NilClass)
+ ```
+
+1. The verification status is stored in the database. To display the database record:
+
+ ```ruby
+ pp X509CommitSignature.by_commit_sha(commit.sha);nil
+ ```
+
+ If all the previous checks returned the correct values:
+
+ - `verification_status: "unverified"` indicates the database record needs
+ updating. [Use the Rake task](#re-verify-commits).
+
+ - `[]` indicates the database doesn't have a record yet. Locate the commit
+ in GitLab to check the signature and store the result.
+
+#### Cryptographic verification checks
+
+If GitLab determines that `verified_signature` is `false`, investigate the reason
+in the Rails console. These checks require `signature` to exist. Refer to the `signature`
+step of the previous [main verification checks](#main-verification-checks).
+
+1. Check the signature, without checking the issuer, returns `true`:
+
+ ```ruby
+ signature.__send__ :valid_signature?
+ ```
+
+1. Check the signing time and date. This check must return `true`:
+
+ ```ruby
+ signature.__send__ :valid_signing_time?
+ ```
+
+ - The code allows for code signing certificates to expire.
+ - A commit must be signed during the validity period of the certificate,
+ and at or after the commit's datestamp. Display the commit time and
+ certificate details including `not_before`, `not_after` with:
+
+ ```ruby
+ commit.created_at
+ pp signature.__send__ :cert; nil
+ ```
+
+1. Check the signature, including that TLS trust can be established. This check must return `true`:
+
+ ```ruby
+ signature.__send__(:p7).verify([], signature.__send__(:cert_store), signature.__send__(:signed_text))
+ ```
+
+ 1. If this fails, add the missing certificate(s) required to establish trust
+ [to the GitLab certificate store](https://docs.gitlab.com/omnibus/settings/ssl.html#install-custom-public-certificates).
+
+ 1. After adding more certificates, (if these troubleshooting steps then pass)
+ run the Rake task to [re-verify commits](#re-verify-commits).
+
+ 1. Display the certificates, including in the signature:
+
+ ```ruby
+ pp signature.__send__(:p7).certificates ; nil
+ ```
+
+Ensure any additional intermediate certificate(s) and the root certificate are added
+to the certificate store. For consistency with how certificate chains are built on
+web servers:
+
+- Git clients that are signing commits should include the certificate
+ and all intermediate certificates in the signature.
+- The GitLab certificate store should only contain the root.
+
+If you remove a root certificate from the GitLab
+trust store, such as when it expires, commit signatures which chain back to that
+root display as `unverified`.