Certificate Authority Rotation

Components of a Teleport cluster authenticate to one another using either X.509 or SSH certificates. To issue certificates, Teleport maintains several certificate authorities. You can rotate Teleport CAs to prevent malicious actors from impersonating part of your Teleport cluster. This guide explains the CAs that Teleport maintains and how to rotate them.

We recommend becoming familiar with the entire guide before following the steps, as you should be ready to roll back the CA rotation if it does not proceed as expected.

How it works

Teleport maintains its CAs independently of one another, and rotating one CA does not affect the rotation status of the others. The rotation process is designed to take place in phases, which give operators time to update their infrastructure and roll back a CA rotation if necessary.

Teleport CA rotation takes place in five phases for each CA. The phases have the following order:

1. standby: No rotation in progress. No operations have begun.
2. init: A new certificate authority is issued, but not used.
3. update_clients: The Teleport Auth Service uses the new CA to sign certificates but continues to trust certificates signed by the original CA.
4. update_servers: Teleport cluster components (Agents, Auth Service, and Proxy Service instances) reload and start serving TLS and SSH certificates signed by the new certificate authority, but still accept certificates issued by the original certificate authority. This only applies to the Teleport host CA.
   1. standby: No rotation in progress. All operations have completed.

Before the final standby phase, you can also put the rotation in the rollback phase, aborting the rotation and returning to the original certificate authority.

CA rotations can be manual or semi-automatic. In manual mode, admins must instruct the Teleport Auth Service to advance from one phase to the next. Between phases, admins can prepare their infrastructure to adjust to each change. In semi-automatic mode, the Teleport Auth Service cycles through each phase automatically, with a grace period between each phase.

Prerequisites

• A running Teleport cluster version 16.4.8 or above. If you want to get started with Teleport, sign up for a free trial or set up a demo environment.

• The tctl admin tool and tsh client tool.

  Visit Installation for instructions on downloading tctl and tsh.

• To check that you can connect to your Teleport cluster, sign in with tsh login, then verify that you can run tctl commands using your current credentials. For example:

  tsh login --proxy=teleport.example.com --user=email@example.com
  tctl status
  Cluster  teleport.example.com
  Version  16.4.8
  CA pin   sha256:abdc1245efgh5678abdc1245efgh5678abdc1245efgh5678abdc1245efgh5678

  If you can connect to the cluster and run the tctl status command, you can use your current credentials to run subsequent tctl commands from your workstation. If you host your own Teleport cluster, you can also run tctl commands on the computer that hosts the Teleport Auth Service for full permissions.

Step 1/4. Choose a CA to rotate

When rotating a CA, you need to check that any infrastructure that relies on the CA has not lost connectivity. You may also need to export the new CA to your infrastructure. Choose one of the CAs below to determine how to keep it up to date during the migration.

We recommend rotating a single CA at a time in order to reduce complexity. The exceptions are the db and db_client CAs, which must be rotated together.

host

The host CA issues certificates to Teleport Agents as well as Auth Service and Proxy Service instances so Teleport clients and the Teleport Auth Service can verify them.

Teleport Agents and Proxy Service instances use heartbeats to periodically report their status to the Teleport Auth Service and update their internal data to reflect data held by the Auth Service. This internal data includes the status of the host CA rotation if one is in progress.

To check the rotation status of an agent or Proxy Service instance, run a variation of the following command:

tctl get resource --format=json | jq '.[] | {hostname: .spec.hostname, rotation: .spec.rotation.state, phase: .spec.rotation.phase}'
{  "hostname": "terminal",  "rotation": "in_progress",  "phase": "init"}

In this example, the Teleport instance named terminal has updated its status to phase init. This means it has downloaded a new CA public key and is ready for state transitions.

You can use the tctl get command with the following resources to determine the rotation state of the host CA on each agent kind:

During each phase of the host CA rotation, make sure all Agents and Proxy Service instances have completed the transition to target phase before proceeding to the next phase. We will explain the phases in Step 2.

If you are joining Teleport processes to a cluster via the Teleport Auth Service, each Teleport process will need a CA pin to trust the Auth Service. The CA pin will change after each host CA rotation. Make sure you use the new CA pin when adding Teleport services after host CA rotation.

user

The user CA issues a certificate when a user authenticates to Teleport. It also signs client certificates for users connecting to Windows desktops and Teleport SSH servers. Teleport-protected servers and Windows desktops use these certificates.

Once you have completed the rotation and reached the final standby phase, users who have signed into Teleport must reauthenticate to receive a user certificate from the new CA, otherwise Teleport client commands fail.

If you have registered Windows desktops with Teleport, follow the guide to export the Teleport user CA so the Windows Desktop Service can authenticate to RDP hosts. Verify that you can connect to registered desktops throughout the rotation.

db and db_client

The db and db_client CAs issue certificates that the Teleport Database Service uses to communicate with self-hosted databases.

The Teleport Database Service presents a certificate signed by the db_client CA when communicating with a self-hosted database, which an admin configures to trust certificates issued by the CA.

Admins can configure self-hosted databases to present a certificate signed by the db CA, which the Database Service uses to verify that a database server is a genuine Teleport-protected resource. Alternatively, self-hosted databases can present a certificate signed by a custom CA, and admins can configure the Teleport Database Service to trust the CA.

Beginning the rotation

The Teleport Database Service starts using client certificates issued by the new CA to connect to databases at the update_clients phase. To avoid losing access to your self-hosted databases in the update_clients phase, you should reconfigure your databases in the init phase, then verify that you can still access your databases after transitioning to the update_clients phase.

Consult the appropriate documentation for configuring your databases before proceeding to the update_clients rotation phase.

At the init phase, the tctl auth sign command differs between the db and db_client CAs. If you rotate the db_client CA, the command outputs both the original and new certificate authorities in its trusted CA output. If you rotate the db CA, the command only issues the new database server certificates.

You do not need to reconfigure databases in the init phase if you are rotating only the db CA, although there is no harm in doing so. If you do not reconfigure databases at this point, you must plan to do so at some point within the rotation, otherwise you will lose access to these databases after transitioning to the final standby phase.

Rolling back the rotation

The most common reason you would want to roll back is if you cannot reconfigure your databases. If you have connectivity issues after reconfiguring a database, it's likely that you misconfigured the database.

If you reconfigured any of your databases during the rotation, you will need to reconfigure them again before transitioning to standby from the rollback phase.

openssh

The openssh CA issues certificates for OpenSSH servers registered with Teleport. Clients verify these certificates when connecting to Teleport-protected OpenSSH servers.

If you used the manual method to enroll any OpenSSH servers, you must follow the instructions to export the openssh CA and provide it to your OpenSSH servers before you transition the rotation to the final standby phase. Otherwise, Teleport users will lose access to any OpenSSH servers you enrolled in your cluster using the manual method.

jwt

The Teleport Auth Service uses the jwt CA to sign JSON web tokens. The Teleport Application Service includes JSON web tokens in HTTP messages that it forwards to Teleport-protected applications, which use the jwt CA to verify the tokens.

If you have enrolled web applications with Teleport, and those applications authenticate traffic from the Teleport Application Service by verifying JSON web tokens against the Teleport certificate authority, you need to ensure that these applications continue to trust the rotated CA.

Teleport-protected JWT applications use one of two methods to retrieve the public key of the Teleport jwt CA. Depending on the method, you may need to take action after the init phase and before the rotation reaches the final standby phase:

• The application queries the /.well-known/jwks.json endpoint of the Teleport Proxy Service. In this case, no action is required as long as the application can continue to access the endpoint. If the application caches jwks.json, invalidate the cache.
• The application accesses the jwks.json file on the local filesystem. Obtain a new jwks.json file by querying the /.well-known/jwks.json endpoint and re-uploading the file.

For an example of exporting the jwt CA so a web application can trust Teleport-issued JWTs, see the guide to using JWT authentication with Elasticsearch.

saml_idp

The saml_idp CA signs SAML messages sent by the Teleport IdP so services that rely on the Teleport IdP can verify them.

If you are rotating this CA, then before entering the final standby phase, you must configure any service providers that rely on the Teleport SAML IdP to trust the Teleport saml_idp CA. Follow the instructions in the SAML IdP documentation to export an XML metadata file and make it available to your service provider.

oidc_idp

The oidc_idp CA signs messages sent by the Teleport OIDC IdP integration. Relying parties (e.g., AWS) verify these messages to authenticate your Teleport account for features like External Audit Storage, Auto-Discovery, and AWS Sync for Access Graph.

The Teleport Proxy Service serves the JSON Web Key Sets for the OIDC IdP integration from the /.well-known/jwks-oidc path of the Web API.

The /.well-known/jwks-oidc path of the Teleport Proxy Service Web API is always enabled. The Teleport Proxy Service updates the endpoint automatically.

You can retrieve the full URL of the integration's JSON Web Key Sets by querying the /.well-known/openid-configuration path of the Web UI and reading the jwks_uri field:

curl https://example.teleport.sh/.well-known/open-id-configuration | jq '.jwks_uri'
"https://example.teleport.sh/.well-known-jwks-oidc"

Step 2/4. Start a manual rotation

Once you have chosen a CA to rotate and have planned to check or update the infrastructure that relies on that CA, you are ready to begin a manual rotation.

init phase

In the init phase, the Teleport Auth Service issues a new certificate authority of the chosen type, but does not use it to sign certificates.

1. Initiate the manual rotation of host certificate authorities:

   tctl auth rotate --manual --type=type --phase=init
   Updated rotation phase to "init". To check status use 'tctl status'

2. Use tctl to confirm that there is an active rotation in progress. This command prints the rotation status of all CAs that the Teleport Auth Service maintains in your cluster:

   tctl status
   Cluster       teleport.example.comVersion       16.4.8host CA       initialized (mode: manual, started: Sep 20 01:44:36 UTC, ending: Sep 21 2023 07:44:36 UTC)user CA       never updateddb CA         never updateddb_client CA  never updatedopenssh CA    never updatedjwt CA        never updatedsaml_idp CA   never updatedoidc_idp CA   never updatedCA pin        sha256:0000000000000000000000000000000000000000000000000000000000000000

3. Perform checks and updates on your infrastructure, depending on the CA type.

update_clients

Execute the transition from init to update_clients. In this phase, The Teleport Auth Service uses the new CA to sign certificates but continues to trust certificates signed by the original CA.

1. Transition to the update_clients phase:

   tctl auth rotate --manual --type=type --phase=update_clients
   Updated rotation phase to "update_clients". To check status use 'tctl status'
   tctl status
   Cluster       teleport.example.comVersion       16.4.8host CA       rotating clients (mode: manual, started: Sep 20 2023 01:44:36 UTC, ending: Sep 21 2023 07:44:36 UTC)user CA       never updateddb CA         never updateddb_client CA  never updatedopenssh CA    never updatedjwt CA        never updatedsaml_idp CA   never updatedoidc_idp CA   never updatedCA pin        sha256:0000000000000000000000000000000000000000000000000000000000000000

2. Check or update infrastructure that depends on your CA before proceeding to the next step.

3. If you lose connectivity to your resources, see if you need to reconfigure them to accept the new CA. If that does not restore access or you are unable to reconfigure a database, then roll back to the original certificate authority.

update_servers

Initiate the update_servers phase. In this phase, Teleport cluster components (Agents, Auth Service, and Proxy Service instances) reload and start serving TLS and SSH certificates signed by the new certificate authority, but still accept certificates issued by the original certificate authority. This phase only affects the host CA.

1. Execute the transition:

   tctl auth rotate --manual --type=type --phase=update_servers
   Updated rotation phase to "update_servers". To check status use 'tctl status'
   
   tctl status
   Cluster       teleport.example.comVersion       16.4.8host CA       rotating servers (mode: manual, started: Sep 20 2023 01:44:36 UTC, ending: Sep 21 2023 07:44:36 UTC)user CA       never updateddb CA         never updateddb_client CA  never updatedopenssh CA    never updatedjwt CA        never updatedsaml_idp CA   never updatedoidc_idp CA   never updatedCA pin        sha256:0000000000000000000000000000000000000000000000000000000000000000

2. Configure and check resources depending on the CA you are rotating. This is your final chance to update Teleport-protected resources before transitioning to the standby phase.

3. If you have lost connectivity to Teleport-protected resources, roll back to the original certificate authority before entering the final standby phase, when rolling back is no longer possible.

Final standby

Before wrapping up, verify that you have not lost access to Teleport-protected resources that rely on the CA that you rotated.

1. Execute the transition:

   tctl auth rotate --manual --type=type --phase=standby

2. Verify that the rotation has completed with tctl:

   tctl status
   Cluster       teleport.example.comVersion       16.4.8host CA       rotated Sep 20 2023 02:11:25 UTCuser CA       never updateddb CA         never updateddb_client CA  never updatedopenssh CA    never updatedjwt CA        never updatedsaml_idp CA   never updatedoidc_idp CA   never updatedCA pin        sha256:0000000000000000000000000000000000000000000000000000000000000000

3. Follow the instructions for your CA to ensure that you can connect to Teleport-protected resources that rely on the CA that you rotated. This is the last stage where you have the opportunity to roll back. If you have lost connectivity to Teleport-protected resources, roll back to the original certificate authority.

Step 3/4. [Optional] Run a semi-automatic rotation

You can instruct Teleport to manage the CA rotation semi-automatically. Semi-automatic rotation transitions between the phases of a rotation for you, and there is no need to run a tctl auth rotate command each phase. After a grace period elapses, the Teleport Auth Service updates the phase of the CA rotation to the next step.

Determine whether to use a semi-automatic rotation

Aside from automatic phase updates, a semi-automatic rotation is identical to a manual one. It is up to the operator to update any infrastructure to accommodate the current phase before the grace period elapses.

Teleport does not check the status of any infrastructure that relies on the CA, meaning that you can lose connectivity if things go wrong. As a result, you should not carry out a semi-automatic rotation if you need to export a CA to your infrastructure.

Complete a rotation in manual mode first to understand all the edge-cases and hazards before attempting a semi-automatic rotation.

Initiate a semi-automatic rotation

If you want to run a semi-automatic rotation, initiate it with tctl and monitor the status of the rotation.

You can trigger semi-automatic rotation with the following command:

tctl auth rotate --type=type

The command triggers a rotation process for hosts with a default grace period of 48 hours.

Rotate only user certificates with a grace period of 200 hours:
tctl auth rotate --type=user --grace-period=200h

Rotate only host certificates with a grace period of 8 hours:
tctl auth rotate --type=host --grace-period=8h

During semi-automatic rotations, Teleport attempts to divide the grace period so that it spends an equal amount of time in each phase before transitioning to the next phase. This means that using a shorter grace period will result in faster state transitions.

Step 4/4. [Optional] Roll back the rotation

You must perform a rollback before the rotation enters standby state.

1. Enter the rollback phase with a manual phase transition:

   tctl auth rotate --phase=rollback --type=type --manual
   Updated rotation phase to "rollback". To check status use 'tctl status'

2. Ensure that you can connect to Teleport resources that depend on the CA you were rotating.

3. Finish rolling back the CA rotation:

   tctl auth rotate --phase=standby --type=type --manual
   Updated rotation phase to "standby". To check status use 'tctl status'

Further reading

How Teleport certificate authorities work.