---
title: "Pinniped v0.25.0: With External Certificate Management for the Impersonation Proxy and more!"
slug: v0-25-0-external-cert-mgmt-impersonation-proxy
date: 2023-08-09
author: Joshua T. Casey
authors: 
- Joshua T. Casey
- Benjamin A. Petersen
image: https://images.unsplash.com/photo-1618075254460-429d47b887c7?ixlib=rb-4.0.3&ixid=M3wxMjA3fDB8MHxwaG90by1wYWdlfHx8fGVufDB8fHx8fA%3D%3D&auto=format&fit=crop&w=2148&q=80
excerpt: "With v0.25.0 you get external certificate management for the impersonation proxy, easier scheduling of the kube-cert-agent, and more"
tags: ['Joshua T. Casey','Ryan Richard', 'Benjamin Petersen', 'release', 'kubernetes', 'pki', 'pinniped', 'tls', 'mtls', 'kind', 'contour', 'cert-manager']
---

![Friendly seal](https://images.unsplash.com/photo-1618075254460-429d47b887c7?ixlib=rb-4.0.3&ixid=M3wxMjA3fDB8MHxwaG90by1wYWdlfHx8fGVufDB8fHx8fA%3D%3D&auto=format&fit=crop&w=2148&q=80)
*Photo by [karlheinz_eckhardt Eckhardt](https://unsplash.com/@karlheinz_eckhardt) on [Unsplash](https://unsplash.com/s/photos/seal)*

With Pinniped v0.25.0 you get the ability to configure an externally-generated certificate for Pinniped Concierge's impersonation proxy to serve TLS.  The
impersonation proxy is a component within Pinniped that allows the project to support many types of clusters, such as 
[Amazon Elastic Kubernetes Service (EKS)](https://aws.amazon.com/eks/), [Google Kubernetes Engine (GKE)](https://cloud.google.com/kubernetes-engine),
and [Azure Kubernetes Service (AKS)](https://azure.microsoft.com/en-us/overview/kubernetes-on-azure).

To read more on this feature, and the design decisions behind it, see the [proposal](https://github.com/vmware-tanzu/pinniped/tree/main/proposals/1547_impersonation-proxy-external-certs).
To read more about the impersonation proxy, see the [docs](https://pinniped.dev/docs/reference/supported-clusters/#background).

To see the feature in practice on a local kind cluster, follow these instructions.
This will perform mTLS between your local client (kubectl and the pinniped CLI) and the impersonation proxy.

The setup: We will be using a kind cluster, Contour as an ingress to the impersonation proxy, and cert-manager to generate a TLS serving cert.
The setup: We will be using a kind cluster, Contour as an ingress to the impersonation proxy, and cert-manager to generate a TLS serving cert.

```shell
Docker desktop v1.20.1
Kind v0.20.0 
Contour v1.25.2
Pinniped v0.25.0
pinniped CLI v0.25.0 (https://pinniped.dev/docs/howto/install-cli/)
cert-manager v1.12.3
````

Set up kind to run with Contour, using the example kind cluster configuration file provided by Contour.

```shell
$ wget https://raw.githubusercontent.com/projectcontour/contour/main/examples/kind/kind-expose-port.yaml
# the --kubeconfig flag on the "create cluster" command will automatically export the kubeconfig file for us
$ kind create cluster \
    --config kind-expose-port.yaml \
    --name kind-with-contour \
    --kubeconfig kind-with-contour.kubeconfig.yaml
```

Now we will install Contour (see https://projectcontour.io/getting-started/ for more details).  Contour provides our kind 
cluster with an Ingress Controller. We will later deploy a Contour HTTPProxy to create DNS that we can 
use to access the impersonation proxy.

```shell
# From https://projectcontour.io/getting-started/
$ kubectl apply \
    --filename https://projectcontour.io/quickstart/contour.yaml \
    --kubeconfig kind-with-contour.kubeconfig.yaml
# Verify that the Contour pods are ready
$ kubectl get pods \
    --namespace projectcontour \
    --output wide \
    --kubeconfig kind-with-contour.kubeconfig.yaml
```

Pinniped's local-user-authenticator will act as a dummy identity provider for our example. This resource is not for production
use but is sufficient for our needs to exercise the new feature of the impersonation proxy. Install Pinniped’s local-user-authenticator 
and add some sample users (see https://pinniped.dev/docs/tutorials/concierge-only-demo/ for more details).

```shell
# Install Pinniped's local-user-authenticator
$ kubectl apply \
    --filename https://get.pinniped.dev/v0.25.0/install-local-user-authenticator.yaml \
    --kubeconfig kind-with-contour.kubeconfig.yaml
# Create a local user "pinny" with password "password123" and group "group-for-mtls".
# Each secret in this namespace acts like a user definition.
$ kubectl create secret generic pinny \
    --namespace local-user-authenticator \
    --from-literal=groups=group-for-mtls \
    --from-literal=passwordHash=$(htpasswd -nbBC 10 x password123 | sed -e "s/^x://") \
    --kubeconfig kind-with-contour.kubeconfig.yaml
# We'll need the CA bundle of the local-user-authenticator service to configure the Concierge's WebhookAuthenticator.
# Just make sure this next command does print out the TLS secret, which can take a few seconds to generate.
$ kubectl get secret local-user-authenticator-tls-serving-certificate \
    --namespace local-user-authenticator \
    --output jsonpath={.data.caCertificate} \
    --kubeconfig kind-with-contour.kubeconfig.yaml \
    | tee local-user-authenticator-ca.pem.b64
```

In this example, we are only interacting with the Pinniped's Concierge. The Supervisor is not in use as we are not interacting 
with a real external OIDC identity provider. Install Pinniped's Concierge:

```shell
$ kubectl apply \
    --filename https://get.pinniped.dev/v0.25.0/install-pinniped-concierge-crds.yaml \
    --kubeconfig kind-with-contour.kubeconfig.yaml

$ kubectl apply \
    --filename https://get.pinniped.dev/v0.25.0/install-pinniped-concierge-resources.yaml \
    --kubeconfig kind-with-contour.kubeconfig.yaml
```

To handle X.509 certificate management for us, we will install cert-manager. For the purposes of this exercise, we will use cert-manager
to generate our CA certificates as well as our TLS serving certificates. Install cert-manager:

```shell
$ kubectl apply \
    --filename https://github.com/cert-manager/cert-manager/releases/download/v1.12.3/cert-manager.yaml \
    --kubeconfig kind-with-contour.kubeconfig.yaml
```

For this demonstration, we will be using cert-manager to simulate our own Public Key Infrastructure (PKI).
We will create the appropriate CA certificates and TLS serving certificates for the impersonation proxy to serve TLS.
For more information about using cert-manager to achieve this, see the [cert-manager docs](https://cert-manager.io/docs/configuration/selfsigned/#bootstrapping-ca-issuers).

In summary, we will do the following:

- Create two `ClusterIssuer` resources, one named `selfsigned-cluster-issuer` and another named `my-ca-issuer`.
- The `ClusterIssuer` named `my-ca-issuer` will be used to create several `Certificate` resources. First, we will create 
  the `Certificate` called `my-selfsigned-ca` (which will reference a `Secret` named `self-signed-ca-for-kind-testing` where
  the actual certificate data will be stored).
- We will later retrieve the `Secret` called `self-signed-ca-for-kind-testing` so that we can add the CA to the Pinniped Concierge's 
  `CredentialIssuer` resource so that it can be advertised and used to verify TLS serving certificates.
- Then, we will create the `ClusterIssuer` called `my-ca-issuer`. We will reference the `Certificate` called `my-selfsigned-ca` via 
  its `Secret` named `self-signed-ca-for-kind-testing`. This will allow us to use the CA to sign TLS serving certificates.
- Then, we will use the `ClusterIssuer` called `my-ca-issuer` to generate a `Certificate` that will be a TLS serving certificate 
  called `impersonation-serving-cert`. As before, the actual certificate data will be stored in a Kubernetes `Secret` which we 
  will name `impersonation-proxy-tls-serving-cert`.
- Finally, we will update the Pinniped Concierge's `CredentiaIissuer` resource to use the TLS serving certificate stored in the 
  `Secret` called `impersonation-proxy-tls-serving-cert`.

If all goes well, the Impersonation Proxy endpoints will be served with a TLS serving certificate that can be validated by the 
CA certificate that generated it.  That's a lot!  Fortunately, the majority of the work is done painlessly via the following 
simple commands:

```shell
$ cat << EOF > self-signed-cert.yaml
---
apiVersion: v1
kind: Namespace
metadata:
  name: cert-manager
---
apiVersion: cert-manager.io/v1
kind: ClusterIssuer
metadata:
  name: selfsigned-cluster-issuer
spec:
  selfSigned: {}
---
apiVersion: cert-manager.io/v1
kind: Certificate
metadata:
  name: my-selfsigned-ca
  namespace: cert-manager
spec:
  isCA: true
  commonName: my-selfsigned-ca
  secretName: self-signed-ca-for-kind-testing
  privateKey:
    algorithm: ECDSA
    size: 256
  issuerRef:
    name: selfsigned-cluster-issuer
    kind: ClusterIssuer
    group: cert-manager.io
---
apiVersion: cert-manager.io/v1
kind: ClusterIssuer
metadata:
  name: my-ca-issuer
spec:
  ca:
    secretName: self-signed-ca-for-kind-testing
---
apiVersion: cert-manager.io/v1
kind: Certificate
metadata:
  name: impersonation-serving-cert
  namespace: pinniped-concierge
spec:
  secretName: impersonation-proxy-tls-serving-cert
  duration: 2160h # 90d
  renewBefore: 360h # 15d
  subject:
    organizations:
    - Pinniped
  isCA: false
  privateKey:
    algorithm: RSA
    encoding: PKCS1
    size: 2048
  usages:
  - server auth
  dnsNames:
  - impersonation-proxy-mtls.local
  issuerRef:
    name: my-ca-issuer
    kind: ClusterIssuer
    group: cert-manager.io

EOF

$ kubectl apply \
    --filename self-signed-cert.yaml \
    --kubeconfig kind-with-contour.kubeconfig.yaml
```

Download the root (self-signed) CA's certificate. We will be adding it to the Pinniped Concierge's `CredentialIssuer` resource 
in order to configure the impersonation proxy to advertise the certificate as its CA.

```shell
$ kubectl get secret self-signed-ca-for-kind-testing \
    --namespace cert-manager \
    --output jsonpath="{.data.ca\.crt}" \
    --kubeconfig kind-with-contour.kubeconfig.yaml \
    | tee self-signed-ca-for-kind-testing.pem.b64
    
# Tip: Put the contents of self-signed-ca-for-kind-testing.pem.b64 into your copy buffer for a later step!
```

The `CredentialIssuer` resource called `pinniped-concierge-config` already exists.  We need to edit it.
Kind clusters do not need to use the impersonation proxy by default (it is designed for public cloud providers),
so we will make several changes to this resource:

- Set the `spec.impersonationProxy.mode: enabled`
- Set the `spec.impersonationProxy.tls.certificateAuthorityData` to match the certificate named `my-ca-issuer` which
  stores its certificate data in the `Secret` called `self-signed-ca-for-kind-testing` (which we previously recorded 
  in the file `self-signed-ca-for-kind-testing.pem.b64`)

```shell
$ kubectl edit credentialissuer pinniped-concierge-config \
    --kubeconfig kind-with-contour.kubeconfig.yaml
```

Make sure that the spec has the following values:

```yaml
  spec:
    impersonationProxy:
      externalEndpoint: impersonation-proxy-mtls.local
      mode: enabled
      service:
        type: ClusterIP
      tls:
        certificateAuthorityData: # paste the contents of the file self-signed-ca-for-kind-testing.pem.b64
        secretName: impersonation-proxy-tls-serving-cert
```

Then save and close the text editor. Once saved, get the resource again and verify that the contents are correct: 

```bash
# Confirm that the CredentialIssuer looks as expected
$ kubectl get credentialissuers pinniped-concierge-config \
    --output yaml \
    --kubeconfig kind-with-contour.kubeconfig.yaml
```

Ensuring the following: 

```yaml
  spec:
    impersonationProxy:
      externalEndpoint: impersonation-proxy-mtls.local
      mode: enabled
      service:
        annotations:
          # Ignore any annotations
        type: ClusterIP
      tls:
        certificateAuthorityData: LS0tLUJFR0l..........
        secretName: impersonation-proxy-tls-serving-cert
  status:
    strategies:
      # this strategy should be automatically updated with the configured 
      # spec.tls.certificateAuthorityData from the previous step
      - frontend:
      impersonationProxyInfo:
        certificateAuthorityData: LS0tLUJFR0l..........
```

In the `CredentialIssuer` `status.strategies` there should be a `frontend` strategy with a `impersonationProxyInfo.certificateAuthorityData`
value that matches that of the configured `spec.tls.certificateAuthorityData`.  This is how the CredentialIssuer advertises
its CA bundle.

Next, we review our `Service` configuration.

```shell
# Confirm that the ClusterIP service for the impersonation proxy was automatically created (may take a minute)
$ kubectl get service pinniped-concierge-impersonation-proxy-cluster-ip \
    --namespace pinniped-concierge \
    --output yaml \
    --kubeconfig kind-with-contour.kubeconfig.yaml
```

Configure a webhook authenticator to tell Concierge to validate static tokens using the installed local-user-authenticator. 
When we installed the Pinniped local-user-authenticator, we created a service called local-user-authenticator in the 
local-user-authenticator namespace. We previously retrieved the Secret named `local-user-authenticator-tls-serving-certificate` 
so that we could use it to configure this `WebhookAuthenticator` to use that certificate. Note that we did not generate this 
certificate via cert-manager, this is still a self-signed certificate created by Pinniped.

The `endpoint` here is referenced via Kubernetes DNS in the format `<namespace>.<service-name>.svc` targeting the `/authenticate` 
endpoint of the local-user-authenticator. We will be using https, if course.

```yaml
# Configure a webhook authenticator to tell Concierge to validate static tokens using the installed local-user-authenticator
$ cat << EOF > concierge.webhookauthenticator.yaml
apiVersion: authentication.concierge.pinniped.dev/v1alpha1
kind: WebhookAuthenticator
metadata:
  name: local-user-authenticator
spec:
  endpoint: https://local-user-authenticator.local-user-authenticator.svc/authenticate
  tls:
    certificateAuthorityData: $(cat local-user-authenticator-ca.pem.b64)
EOF

# Create the webhook authenticator
$ kubectl apply \
    --filename concierge.webhookauthenticator.yaml \
    --kubeconfig kind-with-contour.kubeconfig.yaml
```

Now deploy a Contour `HTTPProxy` ingress that fronts the `ClusterIP` service for the impersonation proxy.

We need to use TLS passthrough in this case, so that the client (kubectl and the pinniped CLI) can establish TLS directly
with the impersonation proxy, and so that client certs used for mTLS will be sent to the impersonation proxy.

Note in particular the `spec.tcpproxy` block, which is different than the typical `spec.rules` block. 
`spec.tcpproxy` is required when using `spec.virtualhost.tls.passthrough: true`. 

See [contour docs for tls session passthrough](https://projectcontour.io/docs/1.25/config/tls-termination/#tls-session-passthrough) for more details.

```shell
$ cat << EOF > contour-ingress-impersonation-proxy.yaml
---
apiVersion: projectcontour.io/v1
kind: HTTPProxy
metadata:
  name: impersonation-proxy
  namespace: pinniped-concierge
spec:
  virtualhost:
    fqdn: impersonation-proxy-mtls.local
    tls:
      passthrough: true
  tcpproxy:
    services:
    - name: pinniped-concierge-impersonation-proxy-cluster-ip
      port: 443
EOF

$ kubectl apply \
    --filename contour-ingress-impersonation-proxy.yaml \
    --kubeconfig kind-with-contour.kubeconfig.yaml
```

Now to generate the Pinniped kubeconfig so that you can perform mTLS with the impersonation proxy.

Since we are interacting with a kind cluster, we will need to ensure HTTP requests are routed to the cluster. 
In this example, we will edit the `/etc/hosts` file to resolve the `impersonation-proxy-mtls.local` to `localhost` via `127.0.0.1`.

```shell
##
# Host Database
127.0.0.1 impersonation-proxy-mtls.local
```

Note that using a static-token does embed those credentials into your kubeconfig. This is not suitable for production 
deployment. As we said before, we are using local-user-authenticator as a simple identity provider for illustrative purposes 
only. In a real production use case you would not employ the `--static-token` flag which would ensure credentials are not 
embedded in your kubeconfig, an important security feature.  Never use local-user-authenticator in production.

```shell
# be sure you added 127.0.0.1 impersonation-proxy-mtls.local to your /etc/hosts!
$ pinniped get kubeconfig \
    --static-token "pinny:password123" \
    --concierge-authenticator-type webhook \
    --concierge-authenticator-name local-user-authenticator \
    --concierge-mode ImpersonationProxy \
    --kubeconfig kind-with-contour.kubeconfig.yaml \
    > pinniped-kubeconfig.yaml
```

Now perform an action as user pinny!

```shell
$ kubectl get pods -A \
    --kubeconfig pinniped-kubeconfig.yaml
Error from server (Forbidden): pods is forbidden: User "pinny" cannot list resource "pods" in API group "" at the cluster scope: decision made by impersonation-proxy.concierge.pinniped.dev
```

This does result in an error because the cluster does not have any `RoleBindings` or `ClusterRoleBindings` that allow your user pinny or the group `group-for-mtls` to perform any actions on the cluster.
Let’s make a `ClusterRoleBinding` that grants this group cluster admin privileges.

```shell
# Perform this as the cluster admin using the kind kubeconfig
$ kubectl create clusterrolebinding mtls-admins \
    --clusterrole=cluster-admin \
    --group=group-for-mtls \
    --kubeconfig kind-with-contour.kubeconfig.yaml
# Now try again with the Pinniped kubeconfig
$ kubectl get pods -A \
    --kubeconfig pinniped-kubeconfig.yaml
NAMESPACE                  NAME                                                      READY   STATUS      RESTARTS       AGE
pinniped-concierge         pinniped-concierge-f4c78b674-bt6zl                        1/1     Running     0              3h36m
```

Congratulations, you have successfully performed mTLS authentication between your local client (kubectl, using the pinniped CLI) 
and the impersonation proxy inside the cluster.

To verify that your username and groups are visible to Kubernetes, run the `pinniped whoami` command.

```shell
pinniped whoami \
    --kubeconfig pinniped-kubeconfig.yaml
```

Finally, verify the expected outcome:

- View the CA embedded in your kubeconfig file: `cat pinniped-kubeconfig.yaml | yq ".clusters[0].cluster.certificate-authority-data"`
- View the CA provided to the impersonation proxy: `kubectl get CredentialIssuer pinniped-concierge-config -o jsonpath="{.status.strategies[1].frontend.impersonationProxyInfo.certificateAuthorityData}"` 
- View the CA we stored in our local PEM file: `cat self-signed-ca-for-kind-testing.pem.b64`