Securing Infrastructure Access at Scale in Large Enterprises
Dec 12
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Run the Jira Access Request Plugin

This guide explains how to set up the Teleport Access Request plugin for Jira. Teleport's Jira integration allows you to manage Teleport Access Requests as Jira issues.

The Teleport Jira plugin synchronizes a Jira project board with the Access Requests processed by your Teleport cluster. When you change the status of an Access Request within Teleport, the plugin updates the board. And when you update the status of an Access Request on the board, the plugin notifies a Jira webhook run by the plugin, which modifies the Access Request in Teleport.

In Teleport Enterprise Cloud, Teleport manages the Mattermost integration for you, and you can enroll the Mattermost integration from the Teleport Web UI.

Visit the Teleport Web UI and on the left sidebar, click Access followed by Integrations. Then click Enroll New Integration to visit the "Enroll New Integration" page:

On the "Select Integration Type" menu, click the tile for your integration. You will see a page with instructions to set up the integration, as well as a form that you can use to configure the integration.

Prerequisites

  • A running Teleport cluster. If you want to get started with Teleport, sign up for a free trial.

  • The tctl admin tool and tsh client tool.

    Visit Installation for instructions on downloading tctl and tsh.

Recommended: Configure Machine ID to provide short-lived Teleport credentials to the plugin. Before following this guide, follow a Machine ID deployment guide to run the tbot binary on your infrastructure.

  • A Jira account with permissions to create applications and webhooks.

  • A registered domain name for the Jira webhook. Jira notifies the webhook of changes in your project board.

  • An environment where you will run the Jira plugin. This is either:

    • A Linux virtual machine with ports 80 and 8081 open, plus a means of accessing the host (e.g., OpenSSH with an SSH port exposed to your workstation).
    • A Kubernetes cluster deployed via a cloud provider. This guide shows you how to allow traffic to the Jira plugin via a LoadBalancer service, so your environment must support services of this type.
  • A means of providing TLS credentials for the Jira webhook run by the plugin. TLS certificates must not be self signed. For example, you can obtain TLS credentials for the webhook with Let's Encrypt by using an ACME client.

    • If you run the plugin on a Linux server, you must provide TLS credentials to a directory available to the plugin.
    • If you run the plugin on Kubernetes, you must write these credentials to a secret that the plugin can read. This guide assumes that the name of the secret is teleport-plugin-jira-tls.
  • 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 17.0.2

    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 1/7. Define RBAC resources

Enable Role Access Requests

Before you set up the Jira plugin, you need to enable Role Access Requests in your Teleport cluster.

For the purpose of this guide, we will define an editor-requester role, which can request the built-in editor role, and an editor-reviewer role that can review requests for the editor role.

Create a file called editor-request-rbac.yaml with the following content:

kind: role
version: v7
metadata:
  name: editor-reviewer
spec:
  allow:
    review_requests:
      roles: ['editor']
---
kind: role
version: v7
metadata:
  name: editor-requester
spec:
  allow:
    request:
      roles: ['editor']
      thresholds:
        - approve: 1
          deny: 1

Create the roles you defined:

tctl create -f editor-request-rbac.yaml
role 'editor-reviewer' has been createdrole 'editor-requester' has been created

Allow yourself to review requests by users with the editor-requester role by assigning yourself the editor-reviewer role.

Assign the editor-reviewer role to your Teleport user by running the appropriate commands for your authentication provider:

  1. Retrieve your local user's roles as a comma-separated list:

    ROLES=$(tsh status -f json | jq -r '.active.roles | join(",")')
  2. Edit your local user to add the new role:

    tctl users update $(tsh status -f json | jq -r '.active.username') \ --set-roles "${ROLES?},editor-reviewer"
  3. Sign out of the Teleport cluster and sign in again to assume the new role.

  1. Open your github authentication connector in a text editor:

    tctl edit github/github
  2. Edit the github connector, adding editor-reviewer to the teams_to_roles section.

    The team you should map to this role depends on how you have designed your organization's role-based access controls (RBAC). However, the team must include your user account and should be the smallest team possible within your organization.

    Here is an example:

      teams_to_roles:
        - organization: octocats
          team: admins
          roles:
            - access
    +       - editor-reviewer
    
  3. Apply your changes by saving closing the file in your editor.

  4. Sign out of the Teleport cluster and sign in again to assume the new role.

  1. Retrieve your saml configuration resource:

    tctl get --with-secrets saml/mysaml > saml.yaml

    Note that the --with-secrets flag adds the value of spec.signing_key_pair.private_key to the saml.yaml file. Because this key contains a sensitive value, you should remove the saml.yaml file immediately after updating the resource.

  2. Edit saml.yaml, adding editor-reviewer to the attributes_to_roles section.

    The attribute you should map to this role depends on how you have designed your organization's role-based access controls (RBAC). However, the group must include your user account and should be the smallest group possible within your organization.

    Here is an example:

      attributes_to_roles:
        - name: "groups"
          value: "my-group"
          roles:
            - access
    +       - editor-reviewer
    
  3. Apply your changes:

    tctl create -f saml.yaml
  4. Sign out of the Teleport cluster and sign in again to assume the new role.

  1. Retrieve your oidc configuration resource:

    tctl get oidc/myoidc --with-secrets > oidc.yaml

    Note that the --with-secrets flag adds the value of spec.signing_key_pair.private_key to the oidc.yaml file. Because this key contains a sensitive value, you should remove the oidc.yaml file immediately after updating the resource.

  2. Edit oidc.yaml, adding editor-reviewer to the claims_to_roles section.

    The claim you should map to this role depends on how you have designed your organization's role-based access controls (RBAC). However, the group must include your user account and should be the smallest group possible within your organization.

    Here is an example:

      claims_to_roles:
        - name: "groups"
          value: "my-group"
          roles:
            - access
    +       - editor-reviewer
    
  3. Apply your changes:

    tctl create -f oidc.yaml
  4. Sign out of the Teleport cluster and sign in again to assume the new role.

Create a user called myuser who has the editor-requester role. This user cannot edit your cluster configuration unless they request the editor role:

tctl users add myuser --roles=editor-requester

tctl will print an invitation URL to your terminal. Visit the URL and log in as myuser for the first time, registering credentials as configured for your Teleport cluster.

Later in this guide, you will have myuser request the editor role so you can review the request using the Teleport plugin.

Create a user and role for the plugin

Teleport's Access Request plugins authenticate to your Teleport cluster as a user with permissions to list, read, and update Access Requests. This way, plugins can retrieve Access Requests from the Teleport Auth Service, present them to reviewers, and modify them after a review.

Define a user and role called access-plugin by adding the following content to a file called access-plugin.yaml:

kind: role
version: v5
metadata:
  name: access-plugin
spec:
  allow:
    rules:
      - resources: ['access_request']
        verbs: ['list', 'read', 'update']
      - resources: ['access_plugin_data']
        verbs: ['update']
---
kind: user
metadata:
  name: access-plugin
spec:
  roles: ['access-plugin']
version: v2

Create the user and role:

tctl create -f access-plugin.yaml

As with all Teleport users, the Teleport Auth Service authenticates the access-plugin user by issuing short-lived TLS credentials. In this case, we will need to request the credentials manually by impersonating the access-plugin role and user.

If you are running a self-hosted Teleport Enterprise deployment and are using tctl from the Auth Service host, you will already have impersonation privileges.

To grant your user impersonation privileges for access-plugin, define a role called access-plugin-impersonator by pasting the following YAML document into a file called access-plugin-impersonator.yaml:

kind: role
version: v5
metadata:
  name: access-plugin-impersonator
spec:
  allow:
    impersonate:
      roles:
      - access-plugin
      users:
      - access-plugin

Create the access-plugin-impersonator role:

tctl create -f access-plugin-impersonator.yaml

Edit your user definition:

TELEPORT_USER=$(tsh status --format=json | jq -r .active.username)
tctl edit users/${TELEPORT_USER?}

Edit your user to include the role you just created:

  roles:
   - access
   - auditor
   - editor
+  - access-plugin-impersonator

Log out of your Teleport cluster and log in again. You will now be able to generate signed certificates for the access-plugin role and user.

Step 2/7. Install the Teleport Jira plugin

Install the Teleport Jira plugin following the instructions below, which depend on whether you are deploying the plugin on a host (e.g., an EC2 instance) or a Kubernetes cluster.

The Teleport Jira plugin must run on a host or Kubernetes cluster that can access both Jira and your Teleport Proxy Service (or Teleport Enterprise Cloud tenant).

Access Request Plugins are available as amd64 and arm64 Linux binaries for downloading. Replace ARCH with your required version.

curl -L -O https://cdn.teleport.dev/teleport-access-jira-v17.0.2-linux-ARCH-bin.tar.gz
tar -xzf teleport-access-jira-v17.0.2-linux-ARCH-bin.tar.gz
cd teleport-access-jira
sudo ./install

Make sure the binary is installed:

teleport-jira version
teleport-jira v17.0.2 git:teleport-jira-v17.0.2-fffffffff go1.22
docker pull public.ecr.aws/gravitational/teleport-plugin-jira:17.0.2

Make sure the plugin is installed by running the following command:

docker run public.ecr.aws/gravitational/teleport-plugin-jira:17.0.2 version
teleport-jira v17.0.2 git:teleport-jira-v17.0.2-api/14.0.0-gd1e081e 1.22

For a list of available tags, visit Amazon ECR Public Gallery.

To install from source you need git and go installed. If you do not have Go installed, visit the Go downloads page.

git clone https://github.com/gravitational/teleport -b branch/v17
cd teleport/integrations/access/jira
git checkout 17.0.2
make

Move the teleport-jira binary into your PATH.

Make sure the binary is installed:

teleport-jira version
teleport-jira v17.0.2 git:teleport-jira-v17.0.2-fffffffff go1.22

Allow Helm to install charts that are hosted in the Teleport Helm repository:

helm repo add teleport https://charts.releases.teleport.dev

Update the cache of charts from the remote repository:

helm repo update

Step 3/7. Export the access plugin identity

Give the plugin access to a Teleport identity file. We recommend using Machine ID for this in order to produce short-lived identity files that are less susceptible to exfiltration, though in demo deployments, you can generate longer-lived identity files with tctl:

Configure tbot with an output that will produce the credentials needed by the plugin. As the plugin will be accessing the Teleport API, the correct output type to use is identity.

For this guide, the directory destination will be used. This will write these credentials to a specified directory on disk. Ensure that this directory can be written to by the Linux user that tbot runs as, and that it can be read by the Linux user that the plugin will run as.

Modify your tbot configuration to add an identity output.

If running tbot on a Linux server, use the directory output to write identity files to the /opt/machine-id directory:

outputs:
- type: identity
  destination:
    type: directory
    # For this guide, /opt/machine-id is used as the destination directory.
    # You may wish to customize this. Multiple outputs cannot share the same
    # destination.
    path: /opt/machine-id

If running tbot on Kubernetes, write the identity file to Kubernetes secret instead:

outputs:
  - type: identity
    destination:
      type: kubernetes_secret
      name: teleport-plugin-slack-identity

If operating tbot as a background service, restart it. If running tbot in one-shot mode, execute it now.

You should now see an identity file under /opt/machine-id or a Kubernetes secret named teleport-plugin-slack-identity. This contains the private key and signed certificates needed by the plugin to authenticate with the Teleport Auth Service.

Like all Teleport users, access-plugin needs signed credentials in order to connect to your Teleport cluster. You will use the tctl auth sign command to request these credentials.

The following tctl auth sign command impersonates the access-plugin user, generates signed credentials, and writes an identity file to the local directory:

tctl auth sign --user=access-plugin --out=identity

The plugin connects to the Teleport Auth Service's gRPC endpoint over TLS.

The identity file, identity, includes both TLS and SSH credentials. The plugin uses the SSH credentials to connect to the Proxy Service, which establishes a reverse tunnel connection to the Auth Service. The plugin uses this reverse tunnel, along with your TLS credentials, to connect to the Auth Service's gRPC endpoint.

By default, tctl auth sign produces certificates with a relatively short lifetime. For production deployments, we suggest using Machine ID to programmatically issue and renew certificates for your plugin. See our Machine ID getting started guide to learn more.

Note that you cannot issue certificates that are valid longer than your existing credentials. For example, to issue certificates with a 1000-hour TTL, you must be logged in with a session that is valid for at least 1000 hours. This means your user must have a role allowing a max_session_ttl of at least 1000 hours (60000 minutes), and you must specify a --ttl when logging in:

tsh login --proxy=teleport.example.com --ttl=60060

If you are running the plugin on a Linux server, create a data directory to hold certificate files for the plugin:

sudo mkdir -p /var/lib/teleport/api-credentials
sudo mv identity /var/lib/teleport/plugins/api-credentials

If you are running the plugin on Kubernetes, Create a Kubernetes secret that contains the Teleport identity file:

kubectl -n teleport create secret generic --from-file=identity teleport-plugin-jira-identity

Once the Teleport credentials expire, you will need to renew them by running the tctl auth sign command again.

Step 4/7. Set up a Jira project

In this section, you will create a Jira a project that the Teleport plugin can modify when a Teleport user creates or updates an Access Request. The plugin then uses the Jira webhook to monitor the state of the board and respond to any changes in the tickets it creates.

Create a project for managing Access Requests

In Jira, find the top navigation bar and click Projects -> Create project. Select Kanban for the template, then Use template. Click Select a company-managed project.

You'll see a screen where you can enter a name for your project. In this guide, we assume that your project is called "Teleport Access Requests", which receives the key TAR by default.

Make sure "Connect repositories, documents, and more" is unset, then click Create project.

In the three-dots menu on the upper right of your new board, click Board settings, then click Columns. Edit the statuses in your board so it contains the following four:

  1. Pending
  2. Approved
  3. Denied
  4. Expired

Create a column with the same name as each status. The result should be the following:

If your project board does not contain these (and only these) columns, each with a status of the same name, the Jira Access Request plugin will behave in unexpected ways. Remove all other columns and statuses.

Click Back to board to review your changes.

Retrieve your Jira API token

Obtain an API token that the Teleport Access Request plugin uses to make changes to your Jira project. Click the gear menu at the upper right of the screen, then click Atlassian account settings. Click Security > Create and manage API tokens > Create API token.

Choose any label and click Copy. Paste the API token into a convenient location (e.g., a password manager or local text document) so you can use it later in this guide when you configure the Jira plugin.

Set up a Jira webhook

Now that you have generated an API key that the Teleport Jira plugin uses to manage your project, enable Jira to notify the Teleport Jira plugin when your project is updated by creating a webhook.

Return to Jira. Click the gear menu on the upper right of the screen. Click System > WebHooks > Create a WebHook.

Enter "Teleport Access Request Plugin" in the "Name" field. In the "URL" field, enter the domain name you created for the plugin earlier, plus port 8081.

Enter "Teleport Access Request Plugin" in the "Name" field. In the "URL" field, enter the domain name you created for the plugin earlier, plus port 443.

The webhook needs to be notified only when an issue is created, updated, or deleted. You can leave all the other boxes empty.

Click Create.

Step 5/7. Configure the Jira Access Request plugin

Earlier, you retrieved credentials that the Jira plugin uses to connect to Teleport and the Jira API. You will now configure the plugin to use these credentials and run the Jira webhook at the address you configured earlier.

Create a configuration file

The Teleport Jira plugin uses a configuration file in TOML format. Generate a boilerplate configuration by running the following command (the plugin will not run unless the config file is in /etc/teleport-jira.toml):

teleport-jira configure | sudo tee /etc/teleport-jira.toml > /dev/null

This should result in a configuration file like the one below:

# Example Jira plugin configuration TOML file
[teleport]
# Proxy Service domain and HTTPS port
auth_server = "myinstance.teleport.sh:443"
# Teleport identity file location
identity = "/var/lib/teleport/plugins/jira/identity"
# Refresh identity file on a periodic basis.
refresh_identity = true

[jira]
url = "https://[my-jira].atlassian.net"    # JIRA URL
username = "bot@example.com"               # JIRA username
api_token = "token"                        # JIRA API token
project = "TAR"                            # JIRA Project key

[http]
# URL on which webhook server is accessible externally, for example,
# [https://]teleport-jira.example.com
public_addr = "example.com" 
https_key_file = "/var/lib/teleport/plugins/jira/server.key"  # TLS private key
https_cert_file = "/var/lib/teleport/plugins/jira/server.crt" # TLS certificate

[log]
output = "stderr" # Logger output. Could be "stdout", "stderr" or "/var/lib/teleport/jira.log"
severity = "INFO" # Logger severity. Could be "INFO", "ERROR", "DEBUG" or "WARN".

The Helm chart for the Jira plugin uses a YAML values file to configure the plugin. On your local workstation, create a file called teleport-jira-helm.yaml based on the following example:

teleport:
  # Teleport Proxy Service domain name and HTTPS port. If you are using Teleport
  # Enterprise Cloud, this should be in the form "your-account.teleport.sh:443"
  address: "teleport.example.com:443"
  # Secret containing a Teleport identity document
  identityFromSecret: teleport-plugin-jira-identity
  # Path within the secret containing the identity file.
  identitySecretPath: identity

jira:
  url: "https://[my-jira].atlassian.net"      # URL of the Jira instance
  username: bot@example.com                   # Email of the bot user
  apiToken: token                             # Token of the bot user
  project: TAR                                # Project where issues will be created

http:
  publicAddress: https://jira-teleport.example.com/ 
  # Secret containing the TLS certificate
  tlsFromSecret: teleport-plugin-jira-tls            
  # tlsKeySecretPath:  tls.key                # Name of the key inside the secret
  # tlsCertSecretPath: tls.crt                # Name of the certificate inside the secret

log:
  output: stderr  # Logger output. Could be "stdout", "stderr" or "/var/lib/teleport/jira.log"
  severity: INFO  # Logger severity. Could be "INFO", "ERROR", "DEBUG" or "WARN".

serviceType: ClusterIP

Edit the configuration file

Open the configuration file created for the Teleport Jira plugin and update the following fields:

[teleport]

The Jira plugin uses this section to connect to your Teleport cluster:

addr: Include the hostname and HTTPS port of your Teleport Proxy Service or Teleport Enterprise Cloud account (e.g., teleport.example.com:443 or mytenant.teleport.sh:443).

identity: Fill this in with the path to the identity file you exported earlier.

client_key, client_crt, root_cas: Comment these out, since we are not using them in this configuration.

address: Include the hostname and HTTPS port of your Teleport Proxy Service or Teleport Enterprise Cloud tenant (e.g., teleport.example.com:443 or mytenant.teleport.sh:443).

identitySecretName: Fill in the identitySecretName field with the name of the Kubernetes secret you created earlier.

identitySecretPath: Fill in the identitySecretPath field with the path of the identity file within the Kubernetes secret. If you have followed the instructions above, this will be identity.

If you are providing credentials to the plugin using a tbot binary that runs on a Linux server, make sure the value of identity is the same as the path of the identity file you configured tbot to generate, /opt/machine-id/identity.

Configure the plugin to periodically reload the identity file, ensuring that it does not attempt to connect to the Teleport Auth Service with expired credentials.

Add the following to the teleport section of the configuration:

refresh_identity = true

jira

url: The URL of your Jira tenant, e.g., https://[your-jira].atlassian.net.

username: The username you were logged in as when you created your API token.

api_token: The Jira API token you retrieved earlier.

project: The project key for your project, which in our case is TAR.

You can leave issue_type as Task or remove the field, as Task is the default.

http

The [http] setting block describes how the plugin's webhook works.

listen_addr indicates the address that the plugin listens on, and defaults to :8081. If you opened port 8081 on your plugin host as we recommended earlier in the guide, you can leave this option unset.

public_addr is the public address of your webhook. This is the domain name you added to the DNS A record you created earlier.

https_key_file and https_cert_file correspond to the private key and certificate you obtained before following this guide. Use the following values, assigning example.com to the domain name you created for the plugin earlier:

  • https_key_file:

    /var/teleport-jira/tls/certificates/acme-v02.api.letsencrypt.org-directory/example.com/example.com.key
  • https_cert_file:

    /var/teleport-jira/tls/certificates/acme-v02.api.letsencrypt.org-directory/example.com/example.com.crt

jira

url: The URL of your Jira tenant, e.g., https://[your-jira].atlassian.net.

username: The username you were logged in as when you created your API token.

apiToken: The API token you retrieved earlier.

project: The project key for your project, which in our case is TAR.

You can leave issueType as Task or remove the field, as Task is the default.

http

The http setting block describes how the plugin's webhook works.

publicAddress: The public address of your webhook. This is the domain name you created for your webhook. (We will create a DNS record for this domain name later.)

tlsFromSecret: The name of a Kubernetes secret containing TLS credentials for the webhook. Use teleport-plugin-jira-tls.

Step 6/7. Run the Jira plugin

After finishing your configuration, you can now run the plugin and test your Jira-based Access Request flow:

Run the following on your Linux host:

sudo teleport-jira start
INFO Starting Teleport Jira Plugin 12.1.1: jira/app.go:112INFO Plugin is ready jira/app.go:142

Install the Helm chart for the Teleport Jira plugin:

helm install teleport-plugin-jira teleport/teleport-plugin-jira \ --namespace teleport \ --values values.yaml \ --version 17.0.2

Create a DNS record that associates the webhook's domain name with the address of the load balancer created by the Jira plugin Helm chart.

See whether the load balancer has a domain name or IP address:

kubectl -n teleport get services/teleport-plugin-jira
NAME TYPE CLUSTER-IP EXTERNAL-IP PORT(S) AGEteleport-plugin-jira LoadBalancer 10.100.135.75 abc123.us-west-2.elb.amazonaws.com 80:30625/TCP,443:31672/TCP 134m

If the EXTERNAL-IP field has a domain name for the value, create a CNAME record in which the domain name for your webhook points to the domain name of the load balancer.

If the EXTERNAL-IP field's value is an IP address, create a DNS A record instead.

You can then generate signed TLS credentials for the Jira plugin, which expects them to be written to a Kubernetes secret.

Check the status of the webhook

Confirm that the Jira webhook has started serving by sending a GET request to the /status endpoint. If the webhook is running, it will return a 200 status code with no document body:

curl -v https://example.com:8081/status 2>&1 | grep "^< HTTP/2"
< HTTP/2 200
curl -v https://example.com:443/status 2>&1 | grep "^< HTTP/2"
< HTTP/2 200

Create an Access Request

Sign in to your cluster as the myuser user you created earlier and create an Access Request:

A Teleport admin can create an Access Request for another user with tctl:

tctl request create myuser --roles=editor

Users can use tsh to create an Access Request and log in with approved roles:

tsh request create --roles=editor
Seeking request approval... (id: 8f77d2d1-2bbf-4031-a300-58926237a807)

Users can request access using the Web UI by visiting the "Access Requests" tab and clicking "New Request":

When you create the request, you will see a new task in the "Pending" column of the Teleport Access Requests board:

Resolve the request

Move the card corresponding to your new Access Request to the "Denied" column, then click the card and navigate to Teleport. You will see that the Access Request has been denied.

Auditing Access Requests

Anyone with access to the Jira project board can modify the status of Access Requests reflected on the board. You can check the Teleport audit log to ensure that the right users are reviewing the right requests.

When auditing Access Request reviews, check for events with the type Access Request Reviewed in the Teleport Web UI.

Step 7/7. Set up systemd

This step is only applicable if you are running the Teleport Jira plugin on a Linux machine.

In production, we recommend starting the Teleport plugin daemon via an init system like systemd. Here's the recommended Teleport plugin service unit file for systemd:

[Unit]
Description=Teleport Jira Plugin
After=network.target

[Service]
Type=simple
Restart=on-failure
ExecStart=/usr/local/bin/teleport-jira start --config=/etc/teleport-jira.toml
ExecReload=/bin/kill -HUP $MAINPID
PIDFile=/run/teleport-jira.pid

[Install]
WantedBy=multi-user.target

Save this as teleport-jira.service or another unit file load path supported by systemd.

sudo systemctl enable teleport-jira
sudo systemctl start teleport-jira