Scaling Privileged Access for Modern Infrastructure: Real-World Insights
Apr 25
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Moderated Sessions

Moderated sessions allow you to define requirements for other users to be present in an active server or Kubernetes session started by another user. Depending on the requirements you specify, users who are allowed to join other users' sessions can be granted permission to do the following:

  • Observe another user's session in real time.
  • Participate interactively in another user's session.
  • Terminate another user's session at will.

The most common use cases for moderated sessions involve the following scenarios:

  • You have strict security or compliance requirements and need to have people watching over user-initiated sessions on a set of servers.
  • You want to share a terminal with someone else to be able to instruct or collaborate.
  • You need the ability to pause or terminate active sessions.

Note that you can share terminal sessions using any Teleport edition. However, you must have Teleport Enterprise or Teleport Enterprise Cloud if you want to require active sessions to be observed or moderated.

Require and allow policies

Moderated sessions use roles to provide fine grained control over who can join a session and who is required to be present to start one.

There are two types of policies you can use to control moderated sessions:

  • Require policies define a set of conditions that must be a met for a session to start or run. A user assigned a role with a require policy must meet the minimum requirements of the policy to start the session that the policy applies to.
  • Allow policies define what sessions users can join and under what conditions they can join a session.

Configure a require policy

In Teleport Enterprise editions, you can use require_session_join in a role to specify the conditions that must be a met for a session to start or run. For example, the following policy specifies that users assigned the prod-access role must have a minimum of one user with the auditor role and the moderator mode present to start SSH or Kubernetes sessions:

kind: role
metadata:
  name: prod-access
version: v7
spec:
  allow:
    require_session_join:
      - name: Auditor oversight
        filter: 'contains(user.spec.roles, "auditor")'
        kinds: ['k8s', 'ssh']
        modes: ['moderator']
        count: 1
    logins:
    - ubuntu
    - debian
    node_labels:
      env: prod
    kubernetes_labels:
      env: prod
    kubernetes_groups:
    - prod-access
    kubernetes_users:
    - USER
    kubernetes_resources:
    - kind: '*'
      name: '*'
      namespace: '*'
      verbs: ['*']

Because this sample policy requires that at least one user with the auditor role to be present as a moderator to start SSH or Kubernetes sessions, a user assigned this prod-access role won't be able to start any sessions on matching resources until the policy requirements are fulfilled.

Required fields

The following are required fields for require_session_join:

OptionTypeDescription
nameStringThe name of the require policy
filterFilterAn expression that, if it evaluates to true for a given user, enables the user to be present in a moderated session.
kindsListThe kind of session—SSH, Kubernetes, or both—that the policy applies to. The valid options are ssh and k8s.
modesListThe participant mode—observer, moderator, or peer—that the user joining the moderated session must match to satisfy the policy.
countIntegerThe minimum number of users that must match the filter expression to satisfy the policy.

Filter expressions

Filter expressions allow for more detailed control over the scope of a policy. For example, you can use a filter expression to specify which users are required to be present in a session. The filter has a user object as its context that you can refine to match the roles and name fields you specify.

In the following example, the filter expression evaluates to true if the user's name is adam or if the user has the role cs-observe:

equals(user.name, "adam") || contains(user.spec.roles, "cs-observe")

Filter expressions support the following functions and operators:

  • contains(set, item): Returns true if the item is in the set, otherwise false. The set can be a string or an array.
  • equals(a, b): Returns true if the two values are equal, otherwise returns false.
  • ![expr]: Negates a Boolean expression.
  • [expr] && [expr]: Performs a logical AND on two Boolean expressions.
  • [expr] || [expr]: Performs a logical OR on two Boolean expressions.

Matching user count

You can use the count field in a require policy to specify the minimum number of users matching the filter expression who must be present in a session to satisfy the policy.

Optional fields

The following field is optional for require_session_join:

OptionTypeDescription
on_leaveStringThe action to take when the policy is no longer satisfied.

You can use the on_leave field in require policies to define what happens when a moderator leaves a session and causes the policy to no longer be satisfied. There are two possible values for this field:

  • terminate to terminate the session immediately and disconnect all participants.
  • pause to pause the session and stop any input/output streaming until the policy is satisfied again.

By default, Teleport treats an empty string in this field the same as terminate.

If all require policies attached to the session owner are set to pause, the session discards all input from session participants and buffers the most recent output but the session remains open so it can resume.

Combining require policies and roles

In evaluating policies and roles, all of the require policies within a role are evaluated using an OR operator and the policies from each role are evaluated using an AND operator. In practice, this means that for every role with at least one require policy, one of its policies must be met before a user assigned the role can start a session.

Requiring moderated sessions in a leaf cluster

If you create a role with the require_session_join policy in a root cluster, only sessions started on resources in the root cluster are required to be moderated for the users assigned that role. If users assigned the role connect to resources in a leaf node, their sessions won't require moderation, unless the mapped leaf role also requires moderation. To require moderated sessions in the leaf cluster, you must include the require_session_join policy in the mapped role defined on the leaf cluster.

For more information about configuring trust relationships and role mapping between root and leaf clusters, see Configure Trusted Clusters.

Configure an allow policy

You can use join_sessions in a role to specify the sessions users can join and under what conditions they can join a session. For example, the following policy is attached to the auditor role and allows a user assigned to the auditor role to join SSH and Kubernetes sessions started by a user with the role prod-access and to join the session as a moderator or an observer:

kind: role
metadata:
  name: auditor
version: v7
spec:
  allow:
    join_sessions:
      - name: Join prod sessions
        roles : ['prod-access']
        kinds: ['k8s', 'ssh']
        modes: ['moderator', 'observer']

Users who are assigned a role with a join_sessions allow policy are implicitly allowed to list the sessions that the policy gives them permission to join. If there's a deny rule that prevents listing sessions, the join_sessions policy overrides the deny rule for the sessions the policy allows the user to join. Outside of this exception for joining sessions, deny statements take precedent.

Required fields

The following are required fields for join_sessions:

OptionTypeDescription
nameStringThe name of the allow policy.
rolesListA list of Teleport role names that the allow policy applies to. Active sessions created by users with these roles can be joined under this policy.
kindsListThe kind of sessions—SSH, Kubernetes, or both—that the allow policy applies to. The valid options are ssh and k8s.
modesListThe participant mode—observer, moderator, or peer—that the user joining the session can use to join the session. The default mode is observer.

Joining a session from the command line

In the following example, Jeff is assigned the prod-access role and attempts to connect to a server in the production environment using tsh ssh:

Teleport > Creating session with ID: 46e2af03-62d6-4e07-a886-43fe741ca044...Teleport > Controls - CTRL-C: Leave the session - t: Forcefully terminate the session (moderators only)Teleport > User jeff joined the session.Teleport > Waiting for required participants...

Jeff's session is paused, waiting for the required observers. When Alice, who is assigned the auditor role, joins the waiting session as a moderator, the session can begin. For example:

tsh join --mode=moderator 46e2af03-62d6-4e07-a886-43fe741ca044
Teleport > Creating session with ID: 46e2af03-62d6-4e07-a886-43fe741ca044...Teleport > Controls - CTRL-C: Leave the session - t: Forcefully terminate the session (moderators only)Teleport > User jeff joined the session.Teleport > Waiting for required participants...Teleport > User alice joined the session.Teleport > Connecting to prod.teleport.example.com over SSH
[email protected] %

Because this session is an SSH session, Alice could also join from the Teleport Web UI. For example:

Participant modes

A participant joining a session will always have one of three modes:

  • observer: Allows read-only access to the session. You can view output but cannot control the session in any way nor send any input.
  • moderator: Allows you to watch the session. You can view output and forcefully terminate or pause the session at any time, but can't send input.
  • peer: Allows you to collaborate in the session. You can view output and send input.

If you join a session with tsh join or tsh kube join, you can specify a participant mode with the --mode <mode> command-line option, where <mode> is peer, moderator, or observer. The default participant mode is observer.

You can leave a session with the shortcut ^c (Control + c) while in observer or moderator mode. In moderator mode, you can also forcefully terminate the session at any point in time with the shortcut t.

Multifactor authentication

If per_session_mfa is set to true in role or cluster settings, Teleport requires multifactor authentication checks when starting new sessions. This requirement is also enforced for session moderators. Therefore, moderators who want to join a session must have configured a device for multifactor authentication.

Every 30 seconds, Teleport prompts session moderators to re-authenticate within the next 15 seconds. This behavior continues throughout the session to ensure that moderators are always present and watching a given session.

If no MFA input is received within 60 seconds, the user is disconnected from the session, which might cause the session to terminate or pause because a require policy is no longer satisfied.

Session kinds

Require and allow policies have to specify which sessions they apply to. Valid options are ssh and k8s.

  • ssh policies apply to all SSH sessions on a node running the Teleport SSH server.
  • k8s policies apply to all Kubernetes sessions on clusters connected to Teleport.

Users with the join_sessions permission for SSH sessions can join sessions from the command line or from the Teleport Web UI. Users with the join_sessions permission for Kubernetes sessions can only join session from the command line.

Session invites

When starting an interactive SSH or Kubernetes session using tsh ssh or tsh kube exec respectively, you can supply the --reason <reason> or --invited <users> command-line option to specify <reason> as a string or <users> as a comma-separated list of user names.

You can use this information to integrate with a third party, for example, to enable notifications over some external communication system.

File transfers

File transfers within moderated sessions are only supported when using the Teleport Web UI. If the current active session requires moderation, file transfer requests are automatically sent to all current session participants.

Both the session originator and the moderator(s) must be present in the Teleport Web UI during the file transfer initiation to receive the file transfer request notification. After the file transfer has been requested, all session participants and notified and prompted to approve or deny the file transfer request.

If a moderator denies the file transfer request, the request is immediately removed and all session participants are notified.

After enough approvals have been given to satisfy the policy used to start the session, the file transfer automatically begins.