SSH certificate injection with HCP Boundary and Vault

20min
|
HCP
Vault
Boundary

HCP Boundary and Boundary Enterprise enable credential injection for SSH certificates into sessions, using the HashiCorp Vault SSH Secrets Engine to dynamically generate certificates. Currently users must bring their own Vault deployment to HCP Boundary.

This tutorial demonstrates SSH certificate injection into an SSH server configured using Docker. Learners may also bring their own target to use for this tutorial.

Tutorial overview

Prerequisites

This tutorial assumes the learner has completed the HCP Boundary Getting Started tutorials. The learner should have a working Boundary cluster and org running on HCP.
Docker is installed (Note: Learners may also bring their own target, instead of using Docker)
A Boundary binary greater than 0.12.0 in your PATH
A Vault binary greater than 1.12.0 in your PATH is recommended. Any version of Vault greater than 1.7 should work with this tutorial.
The jq utility installed and in your PATH
Installing the Boundary Desktop App provides an optional workflow at the end of this tutorial. The 1.2.0 version or above is required for Vault support.

This tutorial assumes basic knowledge of using Vault, including running a development server and managing policies, roles, and tokens. If you are new to using Vault, complete the Getting Started with Vault quick start tutorials before integrating Vault with Boundary.

This tutorial also extends the workflow for credential brokering via Vault. If new to this process, we recommend completing the Vault Credential Brokering Quickstart tutorial before moving forward.

Certificate injection background

SSH, also known as Secure Shell, is arguably the de facto tool for remote administration, enabling end users and administrators with a simple, powerful and secure access method. SSH offers a variety of benefits and configurations, such as:

Encryption
Support for multiple keys types and sizes
Built in key exchange
Ability to create a tunnel and spawn multiple channels

Boundary seamlessly provides authenticated users access to remote machines via their SSH client, regardless of the authentication mechanisms implemented by their administrators.

Boundary supports credential brokering, where Boundary controllers check out credentials from Vault and return them back to users and clients. In this workflow, Boundary acts as a broker of the credential.

Brokering lacks the ability to hide credentials from clients. With credential injection, controllers instead return credentials to Boundary workers and create a session to a target where the client never has access to the credential. This workflow is called credential injection because the credential is injected into a worker’s session, instead of being passed back to the client.

Starting in Boundary 0.10, users can inject SSH private keys, as well as usernames and passwords within Boundary. With public key authentication, keys for each user need to be distributed to all of the correct hosts. In contrast, SSH certificates require administrators to distribute a certificate authority’s (CA) public key to the hosts.

Boundary 0.12 added support for credential injection of Vault SSH certificates. Boundary uses Vault as a certificate authority for SSH certificates by integrating with the Vault SSH Secrets Engine.

Certificate Injection

Boundary administrators can use either the /issue or /sign endpoints to generate certificates from Vault.

This tutorial assumes the reader has installed Boundary 0.12.0 or above, and a Vault binary greater than 1.7.0. Vault can be run in development mode locally, as demonstrated in this tutorial, or by supplying a Vault public address to HCP Boundary.

Set up Vault

Vault needs to be configured to issue certificates for the SSH target. To set up Vault you need to:

Start Vault
Enable the SSH secrets engine
Define the credential and SSH policies
Create a token for the Boundary certificate library
Generate the CA key for signing certificates and add it to Vault

Public or private Vault access is supported by HCP Boundary. If using private Vault or a Vault dev server, a self-managed worker also needs to be deployed. Select one of the options for configuring Vault to continue.

Integrating private Vault with HCP Boundary requires a self-managed worker to be deployed in the same network as Vault. If a Vault credential store is defined with a worker filter, Boundary’s controller will know that Vault requests should be routed to workers matching that filter.

Private Vault On-Premise

Private Vault clusters running on HCP can be configured to access HCP Boundary via a self-managed worker placed in a peered network via a HashiCorp Virtual Network (HCVN).

Private Vault HCPV

For simplicity, this tutorial demonstrates integrating HCP Boundary with a private Vault cluster running locally in development mode with the worker also running locally.

To learn more about HVNs, refer to the HashiCorp Virtual Network documentation.

To learn more about deploying a self-managed worker for HCP, refer to the Self-Managed Worker Registration with HCP Boundary tutorial.

Open a new terminal session and run Vault in development mode.

$ vault server -dev -dev-root-token-id=groot

==> Vault server configuration:

             Api Address: http://127.0.0.1:8200
                     Cgo: disabled
         Cluster Address: https://127.0.0.1:8201
              Go Version: go1.17.13
              Listener 1: tcp (addr: "127.0.0.1:8200", cluster address: "127.0.0.1:8201", max_request_duration: "1m30s", max_request_size: "33554432", tls: "disabled")
               Log Level: info
                   Mlock: supported: false, enabled: false
           Recovery Mode: false
                 Storage: inmem
                 Version: Vault v1.11.4, built 2022-09-23T06:01:14Z
             Version Sha: b47a9e72942719f217f7750df18be36ec21dfc0e

==> Vault server started! Log data will stream in below:

2023-02-12T18:29:53.153-0700 [INFO]  proxy environment: http_proxy="" https_proxy="" no_proxy=""
2023-02-12T18:29:53.153-0700 [WARN]  no `api_addr` value specified in config or in VAULT_API_ADDR; falling back to detection if possible, but this value should be manually set
2023-02-12T18:29:53.155-0700 [INFO]  core: Initializing version history cache for core
2023-02-12T18:29:53.156-0700 [INFO]  core: security barrier not initialized
2023-02-12T18:29:53.156-0700 [INFO]  core: security barrier initialized: stored=1 shares=1 threshold=1
2023-02-12T18:29:53.157-0700 [INFO]  core: post-unseal setup starting
2023-02-12T18:29:53.159-0700 [INFO]  core: loaded wrapping token key
2023-02-12T18:29:53.159-0700 [INFO]  core: Recorded vault version: vault version=1.11.4 upgrade time="2023-02-13 01:29:53.159455 +0000 UTC" build date=2022-09-23T06:01:14Z
2023-02-12T18:29:53.159-0700 [INFO]  core: successfully setup plugin catalog: plugin-directory=""
2023-02-12T18:29:53.159-0700 [INFO]  core: no mounts; adding default mount table
2023-02-12T18:29:53.161-0700 [INFO]  core: successfully mounted backend: type=cubbyhole path=cubbyhole/
2023-02-12T18:29:53.162-0700 [INFO]  core: successfully mounted backend: type=system path=sys/
2023-02-12T18:29:53.162-0700 [INFO]  core: successfully mounted backend: type=identity path=identity/
2023-02-12T18:29:53.164-0700 [INFO]  core: successfully enabled credential backend: type=token path=token/ namespace="ID: root. Path: "
2023-02-12T18:29:53.165-0700 [INFO]  rollback: starting rollback manager
2023-02-12T18:29:53.165-0700 [INFO]  core: restoring leases
2023-02-12T18:29:53.166-0700 [INFO]  identity: entities restored
2023-02-12T18:29:53.166-0700 [INFO]  identity: groups restored
2023-02-12T18:29:53.167-0700 [INFO]  expiration: lease restore complete
2023-02-12T18:29:53.358-0700 [INFO]  core: post-unseal setup complete
2023-02-12T18:29:53.359-0700 [INFO]  core: root token generated
2023-02-12T18:29:53.359-0700 [INFO]  core: pre-seal teardown starting
2023-02-12T18:29:53.359-0700 [INFO]  rollback: stopping rollback manager
2023-02-12T18:29:53.359-0700 [INFO]  core: pre-seal teardown complete
2023-02-12T18:29:53.360-0700 [INFO]  core.cluster-listener.tcp: starting listener: listener_address=127.0.0.1:8201
2023-02-12T18:29:53.360-0700 [INFO]  core.cluster-listener: serving cluster requests: cluster_listen_address=127.0.0.1:8201
2023-02-12T18:29:53.360-0700 [INFO]  core: post-unseal setup starting
2023-02-12T18:29:53.361-0700 [INFO]  core: loaded wrapping token key
2023-02-12T18:29:53.361-0700 [INFO]  core: successfully setup plugin catalog: plugin-directory=""
2023-02-12T18:29:53.361-0700 [INFO]  core: successfully mounted backend: type=system path=sys/
2023-02-12T18:29:53.361-0700 [INFO]  core: successfully mounted backend: type=identity path=identity/
2023-02-12T18:29:53.361-0700 [INFO]  core: successfully mounted backend: type=cubbyhole path=cubbyhole/
2023-02-12T18:29:53.362-0700 [INFO]  core: successfully enabled credential backend: type=token path=token/ namespace="ID: root. Path: "
2023-02-12T18:29:53.362-0700 [INFO]  rollback: starting rollback manager
2023-02-12T18:29:53.362-0700 [INFO]  core: restoring leases
2023-02-12T18:29:53.362-0700 [INFO]  expiration: lease restore complete
2023-02-12T18:29:53.363-0700 [INFO]  identity: entities restored
2023-02-12T18:29:53.363-0700 [INFO]  identity: groups restored
2023-02-12T18:29:53.363-0700 [INFO]  core: post-unseal setup complete
2023-02-12T18:29:53.363-0700 [INFO]  core: vault is unsealed
2023-02-12T18:29:53.365-0700 [INFO]  expiration: revoked lease: lease_id=auth/token/root/h77c55819b7e33ba510334de2c483720207b9da21fbd49582e6b25b400bc6a691
2023-02-12T18:29:53.369-0700 [INFO]  core: successful mount: namespace="" path=secret/ type=kv
2023-02-12T18:29:53.379-0700 [INFO]  secrets.kv.kv_c67682df: collecting keys to upgrade
2023-02-12T18:29:53.379-0700 [INFO]  secrets.kv.kv_c67682df: done collecting keys: num_keys=1
2023-02-12T18:29:53.379-0700 [INFO]  secrets.kv.kv_c67682df: upgrading keys finished
WARNING! dev mode is enabled! In this mode, Vault runs entirely in-memory
and starts unsealed with a single unseal key. The root token is already
authenticated to the CLI, so you can immediately begin using Vault.

You may need to set the following environment variable:

    $ export VAULT_ADDR='http://127.0.0.1:8200'

The unseal key and root token are displayed below in case you want to
seal/unseal the Vault or re-authenticate.

Unseal Key: AfXL/4Tu82hTFkUEHZXrT+3PpuNntoe9NATed3EKke0=
Root Token: groot

Development mode should NOT be used in production installations!

Leave Vault running in dev mode and open a new terminal window.

Next, export the required Vault environment variables for the address and token.

$ export VAULT_ADDR="http://127.0.0.1:8200"; export VAULT_TOKEN="groot"

Then enable the ssh secrets engine at ssh-client-signer/.

$ vault secrets enable -path=ssh-client-signer ssh

Success! Enabled the ssh secrets engine at: ssh-client-signer/

If using HCP Vault Dedicated, gather the public Vault address and generate an Admin token.

HCP URL and Token

Next, export the required Vault environment variables for the address and token.

$ export VAULT_ADDR="https://vault-cluster-boundary.vault.11eb3a47-8920-4714-ba99-0242ac11000e.aws.hashicorp.cloud:8200"; export VAULT_TOKEN="s.mStyhzHOwNsxuLTd5ANWMZ2H.AwVNv"

Vault Dedicated also requires an exported VAULT_NAMESPACE variable. This tutorial demonstrates using the admin namespace.

Export the VAULT_NAMESPACE variable.

$ export VAULT_NAMESPACE=admin

Lastly, enable the ssh secrets engine at ssh-client-signer/.

$ vault secrets enable -path=ssh-client-signer ssh

Success! Enabled the ssh secrets engine at: ssh-client-signer/

Define the controller policy

As described in the Vault Credential Brokering Quickstart tutorial, the following Vault policy must be defined for the Boundary controller to support credential brokering.

Write the controller policy to Vault.

$ vault policy write boundary-controller -<<EOF
path "auth/token/lookup-self" {
  capabilities = ["read"]
}
path "auth/token/renew-self" {
  capabilities = ["update"]
}
path "auth/token/revoke-self" {
  capabilities = ["update"]
}
path "sys/leases/renew" {
  capabilities = ["update"]
}
path "sys/leases/revoke" {
  capabilities = ["update"]
}
path "sys/capabilities-self" {
  capabilities = ["update"]
}
EOF

Define the credential and ssh policies

Vault requires an SSH policy to issue, sign, and update credentials.

Write the ssh policy to Vault.

$ vault policy write ssh -<<EOF
path "ssh-client-signer/issue/boundary-client" {
  capabilities = ["create", "update"]
}

path "ssh-client-signer/sign/boundary-client" {
  capabilities = ["create", "update"]
}
EOF

Lastly, create a role for testing the certificates.

$ vault write ssh-client-signer/roles/boundary-client -<<EOF
{
    "key_type": "ca",
    "allow_user_certificates": true,
    "default_user": "admin",
    "default_extensions": {
        "permit-pty": ""
    },
    "allowed_users": "*",
    "allowed_extensions": "*"
}
EOF

Create a Vault token

Create the a Vault token to be used by Boundary later on, and export it as the $CRED_STORE_TOKEN variable**.

$ export CRED_STORE_TOKEN=$(vault token create \
    -format=json \
    -no-default-policy=true \
    -policy="boundary-controller" \
    -policy="ssh" \
    -orphan=true \
    -period=24h \
    -renewable=true | \
    jq -r '.auth.client_token')

Note

If you plan on using the Admin Console UI to connect, save this value for creating a credential store later on.

$ echo $CRED_STORE_TOKEN
hvs.CAESIL1WVudMz-rmTq5ZofAYPD8Vqgy7g8HC09DGj20CPH-3Gh4KHGh2cy5RZDFKb2NQcGN6V1dsM3ExSzJ2ZEdRNjU

Deploy a self-managed worker

An HCP worker deployed on the same network as Vault is required for integrating private Vault clusters with HCP Boundary. Additionally, a self-managed worker is also needed to route traffic to targets on private networks, like the Docker container in this tutorial. To learn more about setting up self-managed workers, refer to the Self-Managed Worker Registration with HCP Boundary tutorial.

Note

If using both a public Vault endpoint and bringing your own target with a public IP address, skip to the Set up an SSH target section. If bringing your own target on a private network, a self-managed worker must be deployed on the same VPC as the target.

Download the Boundary Enterprise binary

Download the Boundary Enterprise binary to the ~/boundary/ directory.

You can manually download the latest binary for your operating system by navigating to the Boundary releases page. The example below demonstrates downloading the binary using the command line.

Note

The binary version should match the version of the HCP control plane. Check the version of the control plane in the HCP Boundary portal, and download the appropriate version using wget. The example below installs the 0.13.0 version of the Boundary Enterprise binary.

Below is an example of downloading and unzipping the Boundary Enterprise binary on Ubuntu, MacOS, and Windows.

The following command downloads the Boundary Enterprise binary and unzips it to the current directory.

$ wget -q https://releases.hashicorp.com/boundary/0.13.0+ent/boundary_0.13.0+ent_linux_amd64.zip ;\
sudo apt-get update && sudo apt-get install unzip ;\
unzip *.zip

Once downloaded, verify the version of the boundary Boundary.

$ ./boundary version

Version information:
  Build Date:          2023-06-07T16:41:10Z
  Git Revision:        fb4ed58459d555d480e70ddc20d2639c26ad0f8f
  Metadata:            ent
  Version Number:      0.13.0+ent

The following command downloads the Boundary Enterprise binary and unzips it to the current directory.

$ wget -q https://releases.hashicorp.com/boundary/0.13.0+ent/boundary_0.13.0+ent_darwin_amd64.zip ;\
/usr/bin/unzip *.zip

Once downloaded, verify the version of the boundary Boundary.

$ ./boundary version

Version information:
  Build Date:          2023-06-07T16:41:10Z
  Git Revision:        fb4ed58459d555d480e70ddc20d2639c26ad0f8f
  Metadata:            ent
  Version Number:      0.13.0+ent

The following command downloads the Boundary Enterprise binary and unzips it to the current directory.

$ Invoke-WebRequest -OutFile worker.zip https://releases.hashicorp.com/boundary/0.13.0+ent/boundary_0.13.0+ent_windows_amd64.zip ;
Expand-Archive -Path worker.zip -DestinationPath .

Once downloaded, verify the version of the boundary Boundary.

$ .\boundary.exe version

Version information:
  Build Date:          2023-06-07T16:41:10Z
  Git Revision:        fb4ed58459d555d480e70ddc20d2639c26ad0f8f
  Metadata:            ent
  Version Number:      0.13.0+ent

Ensure the Version Number matches the version of the HCP Boundary control plane. They should match in order to get the latest HCP Boundary features.

Write the worker config

Next, open the worker.hcl file with a text editor.

Update the worker config file:

~/boundary/worker.hcl

1 2 3 4 5 6 7 8 9 101112131415disable_mlock = true

hcp_boundary_cluster_id = "<cluster-id>"

listener "tcp" {
  address = "127.0.0.1:9202"
  purpose = "proxy"
}

worker {
  auth_storage_path = "/home/myusername/boundary/worker1"
  tags {
    type = ["worker", "vault"]
  }
}

Update the cluster id in the worker.hcl file:

The <cluster-id> on line 3 can be determined from the UUID in the HCP Boundary Cluster URL. For example, if your Cluster URL is:

https://c3a7a20a-f663-40f3-a8e3-1b2f69b36254.boundary.hashicorp.cloud, then the cluster id is c3a7a20a-f663-40f3-a8e3-1b2f69b36254

The auth_storage_path should match the full path to the ~/boundary/worker1 directory, such as /home/myusername/boundary/worker1.

~/boundary/worker.hcl

1 2 3 4 5 6 7 8 9 101112131415disable_mlock = true

hcp_boundary_cluster_id = "<cluster-id>"

listener "tcp" {
  address = "127.0.0.1:9202"
  purpose = "proxy"
}

worker {
  auth_storage_path = "/Users/myusername/boundary/worker1"
  tags {
    type = ["worker", "vault"]
  }
}

Update the cluster id in the worker.hcl file:

The <cluster-id> on line 3 can be determined from the UUID in the HCP Boundary Cluster URL. For example, if your Cluster URL is:

https://c3a7a20a-f663-40f3-a8e3-1b2f69b36254.boundary.hashicorp.cloud, then the cluster id is c3a7a20a-f663-40f3-a8e3-1b2f69b36254

The auth_storage_path should match the full path to the ~/boundary/worker1 directory, such as /Users/myusername/boundary/worker1.

~/boundary/worker.hcl

1 2 3 4 5 6 7 8 9 101112131415disable_mlock = true

hcp_boundary_cluster_id = "<cluster-id>"

listener "tcp" {
  address = "127.0.0.1:9202"
  purpose = "proxy"
}

worker {
  auth_storage_path = "C:/Users/myusername/boundary/worker1"
  tags {
    type = ["worker", "vault"]
  }
}

Update the cluster id in the worker.hcl file:

The <cluster-id> on line 3 can be determined from the UUID in the HCP Boundary Cluster URL. For example, if your Cluster URL is:

https://c3a7a20a-f663-40f3-a8e3-1b2f69b36254.boundary.hashicorp.cloud, then the cluster id is c3a7a20a-f663-40f3-a8e3-1b2f69b36254

The auth_storage_path should match the full path to the ~/boundary/worker1 directory, such as C:/Users/myusername/boundary/worker1.

Save this file.

Start the worker

With the worker config defined, start the worker server. Provide the full path to the worker config file (such as /home/myusername/boundary/worker.hcl).

1 2 3 4 5 6 7 8 9 101112131415161718$ ./boundary server -config="/home/myusername/boundary/worker.hcl"

==> Boundary server configuration:

                               Cgo: disabled
                        Listener 1: tcp (addr: "127.0.0.1:9202", max_request_duration: "1m30s", purpose: "proxy")
                         Log Level: info
                             Mlock: supported: false, enabled: false
                           Version: Boundary v0.13.0+ent
                       Version Sha: fb4ed58459d555d480e70ddc20d2639c26ad0f8f
        Worker Auth Current Key Id: preaching-favored-verbalize-widen-duchess-relish-jurist-sly
  Worker Auth Registration Request: GzusqckarbczHoLGQ4UA25uSRmUHY1BGSRA6cePp8RWHQFUYSrf3hnDw4ETPswFnMrcxx6tq7BUWD5azGULzPecPicuYGD6qg3qYvaGRgHgKwvh9FLY9Gu891KSj8hAef19JjHog8d7qpo9f9KoiwrhfcV2YxGyVu1P943656iNGCFHWiBR3ofsyTatQ7fzcMV2ciKtuYYGfx4FfiRStnkAzoE98RdR2LeCk2huRkFt7ayeeWVfD7Awm8xaZfFJn4pYRJwu2LRBeNs915warEBaS8XHXSKoi3cRUYif8Qu
          Worker Auth Storage Path: /home/ubuntu/boundary/worker1
          Worker Public Proxy Addr: 127.0.0.1:9202

==> Boundary server started! Log data will stream in below:

{"id":"Rb7PMMBdZa","source":"https://hashicorp.com/boundary/ip-172-31-84-100/worker","specversion":"1.0","type":"system","data":{"version":"v0.1","op":"worker.(Worker).StartControllerConnections","data":{"msg":"Setting HCP Boundary cluster address e58fe114-7624-431c-994d-b6670e90b09f.proxy.boundary.hashicorp.cloud:9202 as upstream address"}},"datacontentype":"application/cloudevents","time":"2022-09-19T22:16:38.770232603Z"}

1 2 3 4 5 6 7 8 9 101112131415161718$ ./boundary server -config="/Users/myusername/boundary/worker.hcl"

==> Boundary server configuration:

                               Cgo: disabled
                        Listener 1: tcp (addr: "127.0.0.1:9202", max_request_duration: "1m30s", purpose: "proxy")
                         Log Level: info
                             Mlock: supported: false, enabled: false
                           Version: Boundary v0.13.0+ent
                       Version Sha: fb4ed58459d555d480e70ddc20d2639c26ad0f8f
        Worker Auth Current Key Id: preaching-favored-verbalize-widen-duchess-relish-jurist-sly
  Worker Auth Registration Request: GzusqckarbczHoLGQ4UA25uSRmUHY1BGSRA6cePp8RWHQFUYSrf3hnDw4ETPswFnMrcxx6tq7BUWD5azGULzPecPicuYGD6qg3qYvaGRgHgKwvh9FLY9Gu891KSj8hAef19JjHog8d7qpo9f9KoiwrhfcV2YxGyVu1P943656iNGCFHWiBR3ofsyTatQ7fzcMV2ciKtuYYGfx4FfiRStnkAzoE98RdR2LeCk2huRkFt7ayeeWVfD7Awm8xaZfFJn4pYRJwu2LRBeNs915warEBaS8XHXSKoi3cRUYif8Qu
          Worker Auth Storage Path: /Users/myusername/boundary/worker1
          Worker Public Proxy Addr: 127.0.0.1:9202

==> Boundary server started! Log data will stream in below:

{"id":"Rb7PMMBdZa","source":"https://hashicorp.com/boundary/ip-172-31-84-100/worker","specversion":"1.0","type":"system","data":{"version":"v0.1","op":"worker.(Worker).StartControllerConnections","data":{"msg":"Setting HCP Boundary cluster address e58fe114-7624-431c-994d-b6670e90b09f.proxy.boundary.hashicorp.cloud:9202 as upstream address"}},"datacontentype":"application/cloudevents","time":"2022-09-19T22:16:38.770232603Z"}

1 2 3 4 5 6 7 8 9 101112131415161718$ .\boundary.exe server -config="C:\Users\myusername\boundary\worker.hcl"

==> Boundary server configuration:

                               Cgo: disabled
                        Listener 1: tcp (addr: "127.0.0.1:9202", max_request_duration: "1m30s", purpose: "proxy")
                         Log Level: info
                             Mlock: supported: false, enabled: false
                           Version: Boundary v0.13.0+ent
                       Version Sha: fb4ed58459d555d480e70ddc20d2639c26ad0f8f
        Worker Auth Current Key Id: preaching-favored-verbalize-widen-duchess-relish-jurist-sly
  Worker Auth Registration Request: GzusqckarbczHoLGQ4UA25uSRmUHY1BGSRA6cePp8RWHQFUYSrf3hnDw4ETPswFnMrcxx6tq7BUWD5azGULzPecPicuYGD6qg3qYvaGRgHgKwvh9FLY9Gu891KSj8hAef19JjHog8d7qpo9f9KoiwrhfcV2YxGyVu1P943656iNGCFHWiBR3ofsyTatQ7fzcMV2ciKtuYYGfx4FfiRStnkAzoE98RdR2LeCk2huRkFt7ayeeWVfD7Awm8xaZfFJn4pYRJwu2LRBeNs915warEBaS8XHXSKoi3cRUYif8Qu
          Worker Auth Storage Path: /Users/myusername/boundary/worker1
          Worker Public Proxy Addr: 127.0.0.1:9202

==> Boundary server started! Log data will stream in below:

{"id":"Rb7PMMBdZa","source":"https://hashicorp.com/boundary/ip-172-31-84-100/worker","specversion":"1.0","type":"system","data":{"version":"v0.1","op":"worker.(Worker).StartControllerConnections","data":{"msg":"Setting HCP Boundary cluster address e58fe114-7624-431c-994d-b6670e90b09f.proxy.boundary.hashicorp.cloud:9202 as upstream address"}},"datacontentype":"application/cloudevents","time":"2022-09-19T22:16:38.770232603Z"}

The worker will start and begin attempting to connect to the upstream Controller.

The worker also outputs its authorization request as the Worker Auth Registration Request token. This will also be saved to a file, auth_request_token, defined by the auth_storage_path in the worker config.

Note the Worker Auth Registration Request: value. This value can also be located in the ~/boundary/worker1/auth_request_token directory. Copy this value.

Register the worker with HCP

Workers can be registered using the Boundary CLI or Admin Console Web UI.

Workers can be registered and managed via the Boundary Admin Web UI.

Authenticate to HCP Boundary as the admin user:

Log in to the HCP portal.
From the HCP Portal's Boundary page, click Open Admin UI - a new page will open.
Enter the admin username and password you created when you deployed the new instance and click Authenticate.

Once logged in, navigate to the Workers page.

Notice that only HCP workers are listed.

Click New.

HCP Workers

Scroll down to the bottom of the New Worker page and paste the Worker Auth Registration Request key you copied earlier.

Click Register Worker.

HCP Workers

Click Done and notice the new worker on the Workers page.

HCP Workers

Ensure that the BOUNDARY_ADDR and BOUNDARY_AUTH_METHOD_ID environment variables are set.

$ export BOUNDARY_ADDR="https://c3a7a20a-f663-40f3-a8e3-1b2f69b36254.boundary.hashicorp.cloud"

$ export BOUNDARY_AUTH_METHOD_ID="ampw_KfLAjMS2CG"

Log into the CLI as the admin user, providing the admin username and password when prompted.

$ boundary authenticate
Please enter the login name (it will be hidden):
Please enter the password (it will be hidden):
Authentication information:
  Account ID:      acctpw_VOeNSFX8pQ
  Auth Method ID:  ampw_wxzojlKJLN
  Expiration Time: Mon, 13 Feb 2023 12:35:32 MST
  User ID:         u_1vUkf5fPs9
The token was successfully stored in the chosen keyring and is not displayed here.

Next, export the Worker Auth Request Token value as an environment variable.

$ export WORKER_TOKEN=<Worker Auth Registration Request Value>

The token is used to issue a create worker request that will authorize the worker to Boundary and make it available. Currently worker creation is only supported for workers with an authorization token.

Now, create the worker:

$ boundary workers create worker-led -worker-generated-auth-token=$WORKER_TOKEN

Worker information:
  Active Connection Count:   0
  Created Time:              Tue, 27 Sep 2022 16:20:21 MDT
  ID:                        w_2yjenAlGvV
  Type:                      pki
  Updated Time:              Tue, 27 Sep 2022 16:20:21 MDT
  Version:                   1

  Scope:
    ID:                      global
    Name:                    global
    Type:                    global

  Authorized Actions:
    no-op
    read
    update
    delete
    add-worker-tags
    set-worker-tags
    remove-worker-tags

Verify the worker details to ensure the worker tags are correctly set.

$ boundary workers read -id w_2yjenAlGvV
Worker information:
  Active Connection Count:   0
  Address:                   127.0.0.1:9202
  Created Time:              Sun, 12 Feb 2023 19:00:44 MST
  ID:                        w_2yjenAlGvV
  Last Status Time:          2023-02-13 04:06:01.548039 +0000 UTC
  Release Version:           Boundary v0.13.0+ent
  Type:                      pki
  Updated Time:              Sun, 12 Feb 2023 21:06:01 MST
  Version:                   1

  Scope:
    ID:                      global
    Name:                    global
    Type:                    global

  Tags:
    Configuration:
      type: ["vault" "worker"]
    Canonical:
      type: ["vault" "worker"]

  Authorized Actions:
    no-op
    read
    update
    delete
    add-worker-tags
    set-worker-tags
    remove-worker-tags

Set up an SSH target

Next, set up a target to test certificate injection using Vault.

Note

Alternatively, you can bring your own target to test the certificate injection. If bringing your own target, expand the accordion below to learn about the settings needed for SSH.

Bring your own target

The example below demonstrates configuring a Debian or RHEL target.

First, generate the CA key for signing certificates and add it to Vault. Note that the jq utility is used to parse the public key. Refer back to the tutorial prerequisites if you need to install jq.

$ vault write -format=json ssh-client-signer/config/ca generate_signing_key=true | \
    jq -r '.data.public_key' > ca/ca-key.pub

The command above has Vault generate a signing certificate, and then jq is used to store the key at ca/ca-key.pub.

Next, set up SSH on the target to trust the CA.

Copy the /ca directory to the target at /ca.

Next, execute the following commands on the target:

$ cp /ca/ca-key.pub /etc/ssh/ca-key.pub \
chown 1000:1000 /etc/ssh/ca-key.pub \
chmod 644 /etc/ssh/ca-key.pub \
echo TrustedUserCAKeys /etc/ssh/ca-key.pub >> /etc/ssh/sshd_config

Lastly, restart ssh.

$ sudo systemctl restart ssh.service

Next, skip to the Set up Boundary section.

Docker is used to deploy an openssh-server target for testing credential injection.

For the purposes of this tutorial, create an ssh keypair that will be used by Vault when signing certificates.

First, open a terminal session and create a new directory to store the keypair in. This tutorial recommends creating the openssh directory within your home directory at ~/, but you can place this directory elsewhere if desired, so long as you deploy the Docker container in the same directory.

$ mkdir openssh/ && cd openssh/

Now create two new directories, ca/ and custom-cont-init.d/.

$ mkdir ca/ && mkdir custom-cont-init.d/

Set up the CA key

Next, generate the CA key for signing certificates and add it to Vault. Note that the jq utility is used to parse the public key. Refer back to the tutorial prerequisites if you need to install jq.

$ vault write -format=json ssh-client-signer/config/ca generate_signing_key=true | \
    jq -r '.data.public_key' > ca/ca-key.pub

The command above has Vault generate a signing certificate, and then jq is used to store the key at ca/ca-key.pub. This directory will be copied onto the docker container target in a moment, so the target has access to the CA's public key.

Next, create a startup script to be used by the open-ssh container. This script sets appropriate permissions on the CA public key so the open-ssh server will trust the Vault CA.

$ cat > custom-cont-init.d/00-trust-user-ca -<<EOF
#!/usr/bin/with-contenv bash

cp /ca/ca-key.pub /etc/ssh/ca-key.pub
chown 1000:1000 /etc/ssh/ca-key.pub
chmod 644 /etc/ssh/ca-key.pub
echo TrustedUserCAKeys /etc/ssh/ca-key.pub >> /etc/ssh/sshd_config
echo PermitTTY yes >> /etc/ssh/sshd_config
sed -i 's/X11Forwarding no/X11Forwarding yes/' /etc/ssh/sshd_config
echo "X11UseLocalhost no" >> /etc/ssh/sshd_config

apk update
apk add xterm util-linux dbus ttf-freefont xauth firefox
EOF

Deploy the target

Ensure Docker is running, and then deploy the openssh container.

Supply the following options to docker run:

The absolute path to the ca/ and custom-cont-init.d/ directories created earlier after the --volume= option,** for example at /Users/myusername/openssh/ca and /Users/myusername/openssh/custom-cont-init.d/.

This will deploy the openssh container and mount the ca/ and custom-cont-init.d/ folder contents as shared volumes.

Update lines 10 and 11 with correct local paths, then execute the following command from the openssh/ directory.

1 2 3 4 5 6 7 8 9 101112$ docker run -d \
--name=openssh-server \
--hostname=openssh-server \
-e SUDO_ACCESS=false \
-e PUID=1000 \
-e PGID=1000 \
-e USER_NAME=admin \
-p 2222:2222 \
--restart unless-stopped \
-v /path/to/ca:/ca \
-v /path/to/custom-cont-init.d/:/custom-cont-init.d \
lscr.io/linuxserver/openssh-server:latest

Note that the username for the openssh server is admin, and the target is available on your localhost at port 2222 (127.0.0.1:2222).

Leave this container running for the duration of the tutorial.

Set up Boundary

Start by logging in to HCP Boundary within the terminal.

Log in to the HCP portal.
From the HCP Portal's Boundary page, click Open Admin UI - a new page will open.
Enter the admin username and password you created when you deployed the new instance and click Authenticate.

Next, set up a new ssh testing org and project scope.

Note

You may use an existing org scope, or create a new org scope for the ssh-project. Refer to the Manage Scopes tutorial to learn more about creating and managing scopes.

Navigate to to the Orgs page and click New Org.
Fill out the new org form with a Name of testing-org and Description of SSH testing org. Click Save.
From within the new org, click New Project.
Fill out the new project form with a Name of ssh-project and Description of SSH test machines. Click Save.

Create a credential store

Next, create a new credential store within Boundary using the new token. The vault credential store type is used for Vault integration, but static credential stores can also be used with credential injection.

Create a new Vault credential store.

Navigate to the Credential Stores page and click New Credential Store.
Fill out the New Credential Store form. Supply the Credential Store Token copied earlier for the Token value:
- Name: certificates-store
- Type: Vault
- Address: http://127.0.0.1:8200
- Worker Filter: "vault" in "/tags/type"
- Token: <CRED_STORE_TOKEN>
Click Save.

Create a new Vault credential store.

Navigate to the Credential Stores page and click New Credential Store.
Fill out the New Credential Store form. Supply the Credential Store Token copied earlier for the Token value, your Vault Dedicated public address, and the Vault Namespace for the Namespace value:
- Name: certificates-store
- Type: Vault
- Address: <HCP_VAULT_PUBLIC_ADDR>
- Token: <CRED_STORE_TOKEN>
- Namespace: <VAULT_NAMESPACE>
Click Save.

Create a credential library

Create a new credential library of type vault-ssh-certificate within Boundary using the credential store ID and passing the vault-path of ssh-client-signer/sign/boundary-client.

Click the newly created certificates-store. Navigate to the Credential Libraries tab. Click the Mange dropdown and select New Credential Library.
Select a Type of SSH Certificates and fill out the New Credential Library form:
- Name: certificates-library
- Type: SSH Certificates
- Vault Path: ssh-client-signer/sign/boundary-client
- Username: admin
- Key Type: ecdsa
- Key Bits: 521
- Extensions: Key: permit-pty
Click Save.

Tip

The Vault ssh-client-signer/sign endpoint can also be used with Vault 1.12.0 and above.

Note

If bringing your own target, update the Username field appropriately, such as ubuntu for an Ubuntu instance.

Vault Cred Library

Create an SSH target

Create a new target of type ssh and set its address to 127.0.0.1 and default port to 2222.

Note

Navigate to the Targets page and click New Target.
Fill out the New Target form. Select a Type of SSH.
- Name: openssh-target
- Type: SSH
- Target Address: 127.0.0.1
- Default Port: 2222
- Maximum Connections: -1
- Egress worker filter: "worker" in "/tags/type"
Click Save.

Note

The Egress worker filter may be omitted if not using a self-managed worker such as when using both a public Vault endpoint and a target with a public IP address.

Now associate the SSH target with the SSH credential library.

Click on the new openssh-target to view its details page.
Select the Injected Application Credentials tab. Click +Add Injected Application Credentials.
Select the certificates-library credential of type SSH Certificates.
Click Add Injected Application Credentials.

Start by logging in to HCP Boundary within the terminal.

Export the BOUNDARY_ADDR environment variable. This value is gathered from the HCP Boundary Admin Console, as demonstrated in the Get Started with HCP Boundary tutorials.

$ export BOUNDARY_ADDR=copied-value-from-hcp-portal

Log in to the CLI as an admin user, or a user with privileges to manage resources in the global scope. Enter your admin username and password when prompted.

$ boundary authenticate
Please enter the login name (it will be hidden):
Please enter the password (it will be hidden):
Authentication information:
  Account ID:      acctpw_VOeNSFX8pQ
  Auth Method ID:  ampw_wxzojlKJLN
  Expiration Time: Mon, 13 Feb 2023 12:35:32 MST
  User ID:         u_1vUkf5fPs9
The token was successfully stored in the chosen keyring and is not displayed here.

You will also need an ORG_ID to create the SSH test project within. You may create a new global scope for this, or utilize an existing scope used for testing.

If creating a new org for testing, execute the following:

$ boundary scopes create -scope-id=global -name=testing-org -description="SSH testing org"

Scope information:
  Created Time:        Mon, 09 May 2022 12:33:12 CDT
  Description:         SSH testing org
  ID:                  o_YcngFcjRcP
  Name:                testing-org
  Updated Time:        Mon, 09 May 2022 12:33:12 CDT
  Version:             1

  Scope (parent):
    ID:                global
    Name:              global
    Type:              global

  Authorized Actions:
    no-op
    read
    update
    delete

Whether you create a new org or not, be sure to export the org ID.

$ export ORG_ID=o_YcngFcjRcP

Set up a new project

Create a new project scope within Boundary. You will need an org ID to create the new project within. To view your existing orgs, execute boundary scopes list -recursive.

Note

You may use an existing org scope, or create a new org scope for the ssh-project. Refer to the Manage Scopes tutorial to learn more about creating and managing scopes.

$ boundary scopes create -scope-id=$ORG_ID -name=ssh-project -description="SSH test machines"

Scope information:
  Created Time:        Fri, 06 May 2022 14:13:39 CDT
  Description:         SSH test machines
  ID:                  p_TRfAEMzkAP
  Name:                ssh-project
  Updated Time:        Fri, 06 May 2022 14:13:39 CDT
  Version:             1

  Scope (parent):
    ID:                o_26VOj9vJjN
    Name:              ssh-org
    Parent Scope ID:   global
    Type:              org

  Authorized Actions:
    no-op
    read
    update
    delete

Copy the ID from the output and export it as the $PROJECT_ID variable.

$ export PROJECT_ID=p_TRfAEMzkAP

Create a credential store

$ boundary credential-stores create vault \
  -scope-id $PROJECT_ID \
  -vault-address $VAULT_ADDR \
  -vault-token $CRED_STORE_TOKEN \
  -worker-filter='"vault" in "/tags/type"'

Example output:

$ boundary credential-stores create vault \
  -name certificates-store \
  -scope-id $PROJECT_ID \
  -vault-address $VAULT_ADDR \
  -vault-token $CRED_STORE_TOKEN \
  -worker-filter='"vault" in "/tags/type"'

Credential Store information:
  Created Time:        Sun, 12 Feb 2023 21:19:35 MST
  ID:                  csvlt_p5Q31jwC3R
  Name:                certificates-store
  Type:                vault
  Updated Time:        Sun, 12 Feb 2023 21:19:35 MST
  Version:             1

  Scope:
    ID:                p_VHAKTCEKcU
    Name:              ssh-project
    Parent Scope ID:   o_FjIYynLyKh
    Type:              project

  Authorized Actions:
    no-op
    read
    update
    delete

  Authorized Actions on Credential Store's Collections:
    credential-libraries:
      create
      list

  Attributes:
    Address:           http://127.0.0.1:8200
    Token HMAC:
    XW6WItywbkR60jzYlV_tNShBGoaUmz5DlVxee9N14bY
    Token Status:      current
    Worker Filter:     "vault" in "/tags/type"

Copy the ID from the output and export it as the $CRED_STORE_ID variable.

$ export CRED_STORE_ID=csvlt_dcpUDG2INd

Tip: If you have the jq utility installed, this can be performed in a single step with this command:

$ export CRED_STORE_ID=`boundary credential-stores create vault -scope-id $PROJECT_ID -vault-address $VAULT_ADDR -vault-token $CRED_STORE_TOKEN -worker-filter='"vault" in "/tags/type"' -format json | jq -r '.item.id'`

Note

If using Vault Dedicated, provide the vault namespace while creating the credential store.

$ boundary credential-stores create vault \
  -scope-id $PROJECT_ID \
  -vault-address $VAULT_ADDR \
  -vault-token $CRED_STORE_TOKEN \
  -vault-namespace $VAULT_NAMESPACE

Example output:

$ boundary credential-stores create vault \
  -name certificates-store \
  -scope-id $PROJECT_ID \
  -vault-address $VAULT_ADDR \
  -vault-token $CRED_STORE_TOKEN \
  -vault-namespace admin

Credential Store information:
  Created Time:        Sun, 12 Feb 2023 21:19:35 MST
  ID:                  csvlt_p5Q31jwC3R
  Name:                certificates-store
  Type:                vault
  Updated Time:        Sun, 12 Feb 2023 21:19:35 MST
  Version:             1

  Scope:
    ID:                p_VHAKTCEKcU
    Name:              ssh-project
    Parent Scope ID:   o_FjIYynLyKh
    Type:              project

  Authorized Actions:
    no-op
    read
    update
    delete

  Authorized Actions on Credential Store's Collections:
    credential-libraries:
      create
      list

  Attributes:
    Address:           https://vault-cluster-boundary.vault.11eb3a47-8920-4714-ba99-0242ac11000e.aws.hashicorp.cloud:8200
    Token HMAC:
    XW6WItywbkR60jzYlV_tNShBGoaUmz5DlVxee9N14bY

Copy the ID from the output and export it as the $CRED_STORE_ID variable.

$ export CRED_STORE_ID=csvlt_dcpUDG2INd

Tip: If you have the jq utility installed, this can be performed in a single step with this command:

$ export CRED_STORE_ID=`boundary credential-stores create vault -scope-id $PROJECT_ID -vault-address $VAULT_ADDR -vault-token $CRED_STORE_TOKEN -vault-namespace admin -format json | jq -r '.item.id'`

Create credential library

Create a new credential library of type vault-ssh-certificate within Boundary using the credential store ID and passing the vault-path of ssh-client-signer/sign/boundary-client.

Note

The sign/ endpoint will work with older versions of Vault. On Vault 1.12 and above, the issue/ endpoint can also be used.

$ boundary credential-libraries create vault-ssh-certificate \
  -name "certificates-library" \
  -credential-store-id $CRED_STORE_ID \
  -vault-path "ssh-client-signer/sign/boundary-client" \
  -username admin \
  -key-type ecdsa \
  -key-bits 521 \
  -extension permit-pty

Example output:

$ boundary credential-libraries create vault-ssh-certificate \
  -name "certificates-library" \
  -credential-store-id $CRED_STORE_ID \
  -vault-path "ssh-client-signer/sign/boundary-client" \
  -username admin \
  -key-type ecdsa \
  -key-bits 521 \
  -extension permit-pty

Credential Library information:
  Created Time:          Sun, 12 Feb 2023 21:43:54 MST
  Credential Store ID:   csvlt_p5Q31jwC3R
  ID:                    clvsclt_NnBsLafvAi
  Name:                  certificates-library
  Type:                  vault-ssh-certificate
  Updated Time:          Sun, 12 Feb 2023 21:43:54 MST
  Version:               1

  Scope:
    ID:                  p_VHAKTCEKcU
    Name:                ssh-project
    Parent Scope ID:     o_FjIYynLyKh
    Type:                project

  Authorized Actions:
    no-op
    read
    update
    delete

  Attributes:
    Extensions:
    {
    "permit-pty": ""
    }
    Key Bits:            521
    Key Type:            ecdsa
    Path:                ssh-client-signer/sign/boundary-client
    Username:            admin

  Credential Type:
    ssh_certificate

Copy the ID from the output and export it as the $CRED_LIB_SSH_ID variable.

$ export CRED_LIB_SSH_ID=clvsclt_VXfc7jsILN

Tip: If you have the jq utility installed, this can be performed in a single step with this command:

$ export CRED_LIB_SSH_ID=`boundary credential-libraries create vault-ssh-certificate -name "certificates-library" -credential-store-id $CRED_STORE_ID -vault-path "secret/data/cred" -username admin -key-type ecdsa -key-bits 521 -extension permit-pty -format json | jq -r '.item.id'`

Create an SSH target

Create a new target of type ssh and set its address to 127.0.0.1 and default port to 2222.

Note

Learners may also bring their own target to test credential injection. If bringing your own target, enter the target's public IP for the -address field, and SSH connection port (likely 22 for SSH) for the -default-port option. The Egress worker filter may be omitted if not using a self-managed worker, such as when using both a public Vault endpoint and a target with a public IP address.

$ boundary targets create ssh -scope-id $PROJECT_ID \
  -name "openssh target" \
  -address 127.0.0.1 \
  -session-connection-limit -1 \
  -default-port 2222 \
  -egress-worker-filter '"worker" in "/tags/type"'

Example output:

$ boundary targets create ssh -scope-id $PROJECT_ID \
  -name "openssh target" \
  -address 127.0.0.1 \
  -session-connection-limit -1 \
  -default-port 2222 /
  -egress-worker-filter '"worker" in "/tags/type"'

Target information:
  Address:                    127.0.0.1
  Created Time:               Sun, 12 Feb 2023 21:34:33 MST
  Egress Worker Filter:       "worker" in "/tags/type"
  ID:                         tssh_1IKJpDJZfL
  Name:                       openssh target
  Session Connection Limit:   -1
  Session Max Seconds:        28800
  Type:                       ssh
  Updated Time:               Sun, 12 Feb 2023 21:34:33 MST
  Version:                    1

  Scope:
    ID:                       p_VHAKTCEKcU
    Name:                     ssh-project
    Parent Scope ID:          o_FjIYynLyKh
    Type:                     project

  Authorized Actions:
    no-op
    read
    update
    delete
    add-host-sources
    set-host-sources
    remove-host-sources
    add-credential-sources
    set-credential-sources
    remove-credential-sources
    authorize-session

  Attributes:
    Default Port:             2222

Copy the ID from the output and export it as the $TARGET_ID variable.

$ export TARGET_ID=tssh_1IKJpDJZfL

Tip: If you have the jq utility installed, this can be performed in a single step with this command:

$ export TARGET_ID=`boundary targets create ssh -scope-id $PROJECT_ID -session-connection-limit=-1 -default-port 2222 -address 127.0.0.1 -name="openssh target" -format json | jq -r '.item.id'`

Now associate the SSH target with the SSH credential library.

$ boundary targets add-credential-sources -id $TARGET_ID -injected-application-credential-source $CRED_LIB_SSH_ID

Target information:
  Address:                    127.0.0.1
  Created Time:               Sun, 12 Feb 2023 21:34:33 MST
  Egress Worker Filter:       "worker" in "/tags/type"
  ID:                         tssh_1IKJpDJZfL
  Name:                       openssh target
  Session Connection Limit:   -1
  Session Max Seconds:        28800
  Type:                       ssh
  Updated Time:               Sun, 12 Feb 2023 21:35:39 MST
  Version:                    2

  Scope:
    ID:                       p_VHAKTCEKcU
    Name:                     ssh-project
    Parent Scope ID:          o_FjIYynLyKh
    Type:                     project

  Authorized Actions:
    no-op
    read
    update
    delete
    add-host-sources
    set-host-sources
    remove-host-sources
    add-credential-sources
    set-credential-sources
    remove-credential-sources
    authorize-session

  Injected Application Credential Sources:
    Credential Store ID:      csvlt_p5Q31jwC3R
    ID:                       clvsclt_VXfc7jsILN

  Attributes:
    Default Port:             2222

Inject certificates into sessions

Now you are ready to inject certificates directly into a shell session. You can accomplish this using the Boundary Desktop App, or by using the boundary connect command.

To log into Boundary using the Desktop App, the BOUNDARY_ADDR (Boundary cluster address) and BOUNDARY_AUTH_METHOD_ID (user Auth Method ID) values must be gathered from the HCP Boundary Admin Console, as demonstrated in the HCP Boundary Getting Started tutorial.

Open the Boundary desktop app.

Enter the Boundary cluster URL (for example, https://ffee961b-5fd8-4e68-ba1d-2bbb487b576e.boundary.hashicorp.cloud) and click Submit.

Authenticate using your HCP Boundary user credentials.

Boundary Desktop Login

Under the Targets page, notice the target details for ssh-target.

Boundary Desktop Target Details

Click Connect to initiate a session.

Boundary Desktop Target Connect

The Successfully Connected page will display the target ID (Target Connection details) and Proxy URL.

To start a session, open your terminal or SSH client. A session can be started using SSH and the Proxy URL from the Boundary desktop app.

For the openssh docker target, connect on 127.0.0.1 and provide the proxy port using the -p option. Enter yes when prompted to establish a connection.

$ ssh 127.0.0.1 -p 51968

The authenticity of host '[127.0.0.1]:2222 ([127.0.0.1]:2222)' can't be established.
ECDSA key fingerprint is SHA256:SzGEXZDM/6u0/9lcO8EDADHXzDsemSFaL6Q36KBrlhQ.
Are you sure you want to continue connecting (yes/no/[fingerprint])? yes
Warning: Permanently added '[127.0.0.1]:2222' (ECDSA) to the list of known hosts.
Welcome to OpenSSH Server

openssh-server:~$

Troubleshooting

If the boundary connect ssh command fails with the following error message, then the Vault credential store token may have expired.

Expand the accordion below to continue troubleshooting.

$ Error from controller when performing authorize-session action against given target

Error information:
  Kind:                FailedPrecondition
  Message:             No egress workers can handle this session, as they have all been filtered
  out.
  Status:              400
  context:             Error from controller when performing authorize-session action against
  given target

Troubleshoot authorize-session error

The error information states that No egress workers can handle this session, as they have all been filtered.

This implies that Boundary does not understand which worker should handle the session, and cannot route traffic through the worker it selected.

In this example the error could be due to either of the following errors:

Boundary is unable to log into Vault using the provided credential store token.
The openssh target's egress worker filter is unset, or incorrect.

First, troubleshoot the Vault credential store by generating a new Vault token.

$ export CRED_STORE_TOKEN=$(vault token create \
  -no-default-policy=true \
  -policy="boundary-controller" \
  -policy="kv-read" \
  -orphan=true \
  -period=20m \
  -renewable=true \
  -field=token) && echo $CRED_STORE_TOKEN

Copy this token (such as hvs.CAESIAbmG5WIi0qILYm87ucbJSGa0rv879aJAchvFR6wG0pbGh4KHGh2cy5xY1BzTGpHUW91ZEx4ZGFTcFVDTkdPMTY), and then update Boundary's Vault cred store with the new token value.

Update the token within the Admin Console UI:

Navigate to the Admin Console in the web browser and authenticate as the admin user.
Navigate to the Credential Stores view within the ssh-project scope.
Click on the certificates-store, and then click on the certificates-library.
Click the Edit Form button in the credential library's details page. Paste the updated CRED_STORE_TOKEN value into the Token field, then click Save.

With an updated Vault credential store token in place, attempt to connect to the target again using the Desktop App.

If you are still unable to establish a connection, check that the worker filter has been defined correctly on the SSH target.

Update the worker filter for the openssh target:

Click on the Targets view within the ssh-project scope.
Click on the openssh target to view its details. Verify that the Egress worker filter switch is toggled on, and the filter matches the following:
```
"worker" in "/tags/type"
```
If incorrect, click the Edit Form button at the bottom of the page and update the filter.
Click Save when finished.

With the updated token in place, attempt to connect to the SSH target again.

When finished, the user can close the connection to the server by entering exit, or the session can be canceled directly from the Boundary desktop app under the Sessions view.

Execute boundary connect, which has a helper called ssh.

Enter yes when prompted to establish the connection.

$ boundary connect ssh -target-id $TARGET_ID

The authenticity of host 'hst_c0ytm16ggf ([127.0.0.1]:49174)' can't be established.
ECDSA key fingerprint is SHA256:+IfWTTBnnsSUSr3ueHjPU8q6jufc9GBDJQVKOIiZzQ4.
Are you sure you want to continue connecting (yes/no/[fingerprint])? yes
Warning: Permanently added 'hst_c0ytm16ggf' (ECDSA) to the list of known hosts.
Welcome to OpenSSH Server

openssh-server:~$

Troubleshooting

If the boundary connect ssh command fails with the following error message, then the Vault credential store token may have expired.

Expand the accordion below to continue troubleshooting.

$ Error from controller when performing authorize-session action against given target

Error information:
  Kind:                FailedPrecondition
  Message:             No egress workers can handle this session, as they have all been filtered
  out.
  Status:              400
  context:             Error from controller when performing authorize-session action against
  given target

Troubleshoot authorize-session error

The error information states that No egress workers can handle this session, as they have all been filtered.

This implies that Boundary does not understand which worker should handle the session, and cannot route traffic through the worker it selected.

In this example the error could be due to either of the following errors:

Boundary is unable to log into Vault using the provided credential store token.
The openssh target's egress worker filter is unset, or incorrect.

First, troubleshoot the Vault credential store by generating a new Vault token.

$ export CRED_STORE_TOKEN=$(vault token create \
  -no-default-policy=true \
  -policy="boundary-controller" \
  -policy="kv-read" \
  -orphan=true \
  -period=20m \
  -renewable=true \
  -field=token) && echo $CRED_STORE_TOKEN

Copy this token (such as hvs.CAESIAbmG5WIi0qILYm87ucbJSGa0rv879aJAchvFR6wG0pbGh4KHGh2cy5xY1BzTGpHUW91ZEx4ZGFTcFVDTkdPMTY), and then update Boundary's Vault cred store with the new token value.

Update the vault credential store's token, and ensure that the worker filter has been correctly defined.

$ boundary credential-stores update vault \
  -id $CRED_STORE_ID \
  -vault-token $CRED_STORE_TOKEN \
  -worker-filter='"vault" in "/tags/type"'

With the updated token in place, attempt to connect to the SSH target again.

If you are still unable to establish a connection, check that the filter has been defined correctly on the SSH target.

Read the details of the openssh target:

$ boundary targets read -id $TARGET_ID

Target information:
  Address:                    127.0.0.1
  Created Time:               Sun, 12 Feb 2023 21:34:33 MST
  Egress Worker Filter:       "worker" in "/tags/type"
  ID:                         tssh_1IKJpDJZfL
  Name:                       openssh target
  Session Connection Limit:   -1
  Session Max Seconds:        28800
  Type:                       ssh
  Updated Time:               Sun, 12 Feb 2023 21:35:39 MST
  Version:                    2

  Scope:
    ID:                       p_VHAKTCEKcU
    Name:                     ssh-project
    Parent Scope ID:          o_FjIYynLyKh
    Type:                     project

  Authorized Actions:
    no-op
    read
    update
    delete
    add-host-sources
    set-host-sources
    remove-host-sources
    add-credential-sources
    set-credential-sources
    remove-credential-sources
    authorize-session

  Injected Application Credential Sources:
    Credential Store ID:      csvlt_p5Q31jwC3R
    ID:                       clvsclt_VXfc7jsILN

  Attributes:
    Default Port:             2222

Check that the Egress worker filter in the output matches the following:

"worker" in "/tags/type"

If this is missing or incorrect, update the target with the correct filter:

$ boundary targets update ssh \
  -id $TARGET_ID \
  -egress-worker-filter '"worker" in "/tags/type"'

When finished, the user can close the connection to the server using exit, or the session can be canceled directly from Boundary in a new terminal window:

$ boundary sessions list -recursive

Session information:
  ID:                    s_EOsEgwF3JN
    Scope ID:            p_ZbpoZDE03L
    Status:              active
    Created Time:        Mon, 09 May 2022 12:39:02 CDT
    Expiration Time:     Mon, 09 May 2022 20:39:01 CDT
    Updated Time:        Mon, 09 May 2022 12:39:02 CDT
    User ID:             u_1234567890
    Target ID:           tssh_zIUXGVzB5L
    Authorized Actions:
      no-op
      read
      read:self
      cancel
      cancel:self

Copy the session ID and cancel the session:

$ boundary sessions cancel -id s_EOsEgwF3JN

Session information:
  Auth Token ID:       at_wXd9EASFp6
  Created Time:        Mon, 09 May 2022 12:39:02 CDT
  Endpoint:            ssh://127.0.0.1:2222
  Expiration Time:     Mon, 09 May 2022 20:39:01 CDT
  Host ID:             hst_C0YtM16ggf
  Host Set ID:         hsst_DyUCqhHuiP
  ID:                  s_EOsEgwF3JN
  Status:              canceling
  Target ID:           tssh_zIUXGVzB5L
  Type:                ssh
  Updated Time:        Mon, 09 May 2022 12:43:28 CDT
  User ID:             u_1234567890
  Version:             3

  Scope:
    ID:                p_ZbpoZDE03L
    Name:              ssh-project
    Parent Scope ID:   o_YcngFcjRcP
    Type:              project

  Authorized Actions:
    no-op
    read
    read:self
    cancel
    cancel:self

  States:
    Start Time:        Mon, 09 May 2022 12:43:28 CDT
    Status:            canceling

    End Time:          Mon, 09 May 2022 12:43:28 CDT
    Start Time:        Mon, 09 May 2022 12:39:02 CDT
    Status:            active

    End Time:          Mon, 09 May 2022 12:39:02 CDT
    Start Time:        Mon, 09 May 2022 12:39:02 CDT
    Status:            pending

You can verify the session was canceled by listing the sessions again and noticing the terminated Status:

$ boundary sessions list -recursive

Session information:
  ID:                    s_EOsEgwF3JN
    Scope ID:            p_ZbpoZDE03L
    Status:              terminated
    Created Time:        Mon, 09 May 2022 12:39:02 CDT
    Expiration Time:     Mon, 09 May 2022 20:39:01 CDT
    Updated Time:        Mon, 09 May 2022 12:43:29 CDT
    User ID:             u_1234567890
    Target ID:           tssh_zIUXGVzB5L
    Authorized Actions:
      no-op
      read
      read:self
      cancel
      cancel:self

Note

In addition to injecting SSH credentials, brokered credentials can also be passed to the user if they are attached to the target. This can be useful when the user needs access to application credentials once they are connected to the target.

Note

There are cases in which targets might have multiple SSH keys or username_password credentials attached as injected application credential sources. SSH supports multiple credential sources, and Boundary will try them until it finds a usable credential when attempting a connection. This scenario is useful when rotating private keys. Both the old key and the new key can be attached to a target simultaneously, and Boundary will try both of them, stopping if one is successful. This facilitates key rotation without downtime.

Testing X11 forwarding (optional)

The openssh-server container is configured to allow X11 forwarding, but the credential library must be configured to permit X11 forwarding.

$ boundary credential-libraries update vault-ssh-certificate \
    -id $CRED_LIB_SSH_ID \
    -extension permit-pty \
    -extension permit-X11-forwarding

Then, boundary connect can pass through the -X option.

$ boundary connect ssh -target-id $TARGET_ID -- -X

Welcome to OpenSSH Server

openssh-server:~$

Testing critical options (optional)

The openssh-server container is configured to allow critical options, but the credential library must be configured to permit them.

$ boundary credential-libraries update vault-ssh-certificate \
    -id $CRED_LIB_SSH_ID \
    -critical-option force-command=bc

Then, boundary connect will use the critical option.

$ boundary connect ssh -target-id $TARGET_ID

bc 1.35.0
Adapted from https://github.com/gavinhoward/bc
Original code (c) 2018 Gavin D. Howard and contributors

Force-close the connection with ctrl+c when finished.

To combine with X11 forwarding:

$ boundary credential-libraries update vault-ssh-certificate \
    -id $CRED_LIB_SSH_ID \
    -extension permit-pty \
    -extension permit-X11-forwarding \
    -critical-option force-command='firefox https://www.boundaryproject.io/'

Then, boundary connect can read the Boundary docs through Boundary:

$ boundary connect ssh -target-id $TARGET_ID -- -X

Note

To test this on macOS, you likely need to install XQuartz.

Cleanup and teardown

Locate the terminal session used to execute the vault dev server command, and execute ctrl+c to stop Vault.

Unset the environment variables used in any active terminal windows for this tutorial.

$ unset VAULT_ADDR; unset VAULT_TOKEN

Destroy the openssh-server container created for the tutorial.

$ docker rm -f openssh-server

Check your work by executing docker ps and ensure there are no more containers from the tutorial leftover. If unexpected containers still exist, execute docker rm -f <CONTAINER_ID> against each to remove them.

Tutorial overview

Prerequisites

Certificate injection background

Set up Vault

Define the controller policy

Define the credential and ssh policies

Create a Vault token

Deploy a self-managed worker

Download the Boundary Enterprise binary

Write the worker config

Start the worker

Register the worker with HCP

Set up an SSH target

Set up the CA key

Deploy the target

Set up Boundary

Create a credential store

Create a credential library

Create an SSH target

Inject certificates into sessions

Cleanup and teardown

Help and reference