# Authentik deployment checklist

## Purpose

This runbook is the operator path for deploying, verifying, and handing off
Authentik as the homelab identity provider.

It covers:

- Preflight checks: secrets, Swarm state, storage, and network readiness.
- Deployment execution using the canonical Ansible playbook.
- Service convergence and health verification.
- Ingress and functional smoke tests against the live endpoint.
- Post-deploy hardening, evidence capture, and rollback guidance.
- Day-1 troubleshooting for common failure modes.

## Scope

- **Stack name:** `authentik`
- **Canonical playbook:** `ansible/playbooks/docker/deploy_authentik.yml`
- **Stack template:** `ansible/templates/stacks/authentik.stack.yml`
- **Target manager:** `swarm-manager-1` (`10.0.0.211`)
- **Public URL:** `https://sso.castaldifamily.com`
- **Data root:** `/mnt/homelab/apps/authentik`
- **Services deployed:** `authentik-postgres`, `authentik-redis`, `authentik-server`, `authentik-worker`

> [!IMPORTANT]
> This stack uses **absolute bind mounts**. The deploy playbook requires all data
> directories to exist before deployment. If any path is missing, the preflight
> asserts will fail-safe and abort rather than bootstrap an empty installation
> over existing data.

---

## Deployment flow

```mermaid
flowchart LR
    preflight[Phase 1 — Preflight] --> validation[Phase 2 — Validation run]
    validation --> deploy[Phase 3 — Deploy]
    deploy --> convergence[Phase 4 — Convergence]
    convergence --> ingress[Phase 5 — Ingress checks]
    ingress --> handoff[Phase 6 — Handoff]

    classDef phase fill:#dbeafe,stroke:#3b82f6;
    class preflight,validation,deploy,convergence,ingress,handoff phase
```

---

## Phase 1 — Preflight checklist

Complete all items in this phase before running any playbook command.

### 1.1 Change window and ownership

- [ ] Deployment owner is assigned.
- [ ] Rollback owner is assigned.
- [ ] Maintenance window is confirmed.
- [ ] No active cluster incidents in the latest Swarm audit
      (`outputs/swarm_audit_*.md`).

### 1.2 Control node readiness

Run from the `ansible/` directory with the virtual environment active.

```bash
# Confirm Python environment
source /home/chester/homelab/.venv/bin/activate

# Confirm Ansible version (must be >= 2.18.0)
ansible --version

# Confirm SSH access to all Swarm managers
ansible swarm_managers -i inventory/hosts.ini -m ping
```

- [ ] Ansible version is `2.18.0` or higher.
- [ ] All Swarm managers return `pong`.
- [ ] Vault password is available (`.vault_pass` file present or `ANSIBLE_VAULT_PASSWORD_FILE` set).

### 1.3 Secrets readiness

The deploy playbook asserts both values are defined, non-empty, and not
placeholder strings. Verify them first:

```bash
ansible -i inventory/hosts.ini localhost \
  -m ansible.builtin.debug \
  -a "msg={{ vault_authentik_secret_key | length }}" \
  -e "@group_vars/all.yml" \
  --vault-password-file .vault_pass
```

Repeat for `vault_authentik_postgres_password`.

- [ ] `vault_authentik_secret_key` decrypts to a non-empty, non-placeholder value.
- [ ] `vault_authentik_postgres_password` decrypts to a non-empty, non-placeholder value.
- [ ] Neither value is any of: `change-me`, `changeme`, `your-random-secret`, `your-db-password`.

### 1.4 Swarm cluster state

```bash
# Confirm target manager is active and is control-plane
ssh chester@10.0.0.211 \
  "docker info --format '{{.Swarm.LocalNodeState}}|{{.Swarm.ControlAvailable}}'"
# Expected output: active|true

# Confirm all managers are active
ansible swarm_managers -i inventory/hosts.ini \
  -m ansible.builtin.command \
  -a "docker info --format '{{.Swarm.LocalNodeState}}'"
```

- [ ] `swarm-manager-1` returns `active|true`.
- [ ] All three managers return `active`.
- [ ] No node shows `inactive`, `pending`, or `error`.

### 1.5 External overlay network

Authentik requires `proxy-net` to exist before stack deploy.

```bash
ssh chester@10.0.0.211 \
  "docker network ls --filter name=proxy-net --format '{{.Name}}|{{.Driver}}|{{.Scope}}'"
# Expected: proxy-net|overlay|swarm
```

- [ ] `proxy-net` exists with `overlay` driver and `swarm` scope.

> [!WARNING]
> If `proxy-net` is missing, create it before continuing:
> ```bash
> ssh chester@10.0.0.211 \
>   "docker network create --driver overlay --attachable proxy-net"
> ```

### 1.6 Persistent data paths

All bind-mount paths must exist on `swarm-manager-1` **before** deploying.
The playbook will fail-safe if any are missing.

```bash
ssh chester@10.0.0.211 "for d in \
  /mnt/homelab/apps/authentik \
  /mnt/homelab/apps/authentik/data \
  /mnt/homelab/apps/authentik/data/database \
  /mnt/homelab/apps/authentik/data/redis \
  /mnt/homelab/apps/authentik/data/media \
  /mnt/homelab/apps/authentik/data/config \
  /mnt/homelab/apps/authentik/data/blueprints; do
    [ -d \"\$d\" ] && echo \"OK  \$d\" || echo \"MISSING  \$d\"
done"
```

- [ ] All 7 paths return `OK`.
- [ ] If any path is `MISSING`, create or restore from backup before proceeding.

To create paths for a **fresh install** (no existing data to protect):

```bash
ssh chester@10.0.0.211 "sudo mkdir -p \
  /mnt/homelab/apps/authentik/data/database \
  /mnt/homelab/apps/authentik/data/redis \
  /mnt/homelab/apps/authentik/data/media \
  /mnt/homelab/apps/authentik/data/config \
  /mnt/homelab/apps/authentik/data/blueprints"
```

> [!WARNING]
> Do not create missing paths if you are restoring an existing Authentik install.
> Restore from backup first to avoid initialising an empty database over
> pre-existing data.

---

## Phase 2 — Validation-only run

Run the playbook in validation mode to confirm all asserts pass before
changing anything on the cluster.

```bash
cd /home/chester/homelab/ansible

ansible-playbook \
  -i inventory/hosts.ini \
  playbooks/docker/deploy_authentik.yml \
  -e "stack_validate_only=true" \
  --vault-password-file .vault_pass
```

- [ ] Playbook completes with `0` failed tasks.
- [ ] Secrets assertion tasks pass (no `FAILED` on assert blocks).
- [ ] Swarm manager state assertion passes.
- [ ] Data path assertions pass for all 7 required directories.

**Stop here if any assert fails.** Diagnose using the
[Troubleshooting matrix](#troubleshooting-matrix) below, then re-run validation
before proceeding.

---

## Phase 3 — Deployment execution

Run the standard deploy. All playbook output should be captured for the
evidence record.

```bash
cd /home/chester/homelab/ansible

ansible-playbook \
  -i inventory/hosts.ini \
  playbooks/docker/deploy_authentik.yml \
  --vault-password-file .vault_pass \
  2>&1 | tee ../outputs/authentik_deploy_$(date +%Y%m%dT%H%M%S).log
```

- [ ] Playbook completes without `FAILED` tasks.
- [ ] Deployment result block is printed confirming stack name, manager, and URL.
- [ ] Log file is saved to `outputs/` with a timestamp.

**Expected deployment result output:**

```
"Authentik deployment complete."
"Stack     : authentik"
"Manager   : swarm-manager-1 (10.0.0.211)"
"URL       : https://sso.castaldifamily.com"
"Data root : /mnt/homelab/apps/authentik"
"Services  : authentik-postgres, authentik-redis, authentik-server, authentik-worker"
```

---

## Phase 4 — Service convergence and health

Verify that all four services are running, stable, and healthy.

### 4.1 Service replica status

```bash
ssh chester@10.0.0.211 \
  "docker service ls --filter label=com.docker.stack.namespace=authentik"
```

Expected replica counts:

| Service | Expected |
| :--- | :---: |
| `authentik_authentik-postgres` | `1/1` |
| `authentik_authentik-redis` | `1/1` |
| `authentik_authentik-server` | `1/1` |
| `authentik_authentik-worker` | `1/1` |

- [ ] All four services show `1/1` replicas.
- [ ] No service shows `0/1` or a failure count.

### 4.2 Service placement

All four services must be pinned to `swarm-manager-1`.

```bash
ssh chester@10.0.0.211 \
  "docker service ps authentik_authentik-server --filter desired-state=running --format '{{.Node}} {{.CurrentState}}'"
# Expected: swarm-manager-1   Running ...
```

- [ ] `authentik-server` task is running on `swarm-manager-1`.
- [ ] `authentik-worker` task is running on `swarm-manager-1`.

### 4.3 Container health checks

```bash
# postgres health (pg_isready)
ssh chester@10.0.0.211 \
  "docker ps --filter name=authentik_authentik-postgres --format '{{.Status}}'"
# Expected: Up ... (healthy)

# redis health (redis-cli ping)
ssh chester@10.0.0.211 \
  "docker ps --filter name=authentik_authentik-redis --format '{{.Status}}'"
# Expected: Up ... (healthy)
```

- [ ] `authentik-postgres` container shows `(healthy)`.
- [ ] `authentik-redis` container shows `(healthy)`.

### 4.4 Critical startup log checks

```bash
# Check server startup for migration and database connectivity
ssh chester@10.0.0.211 \
  "docker service logs authentik_authentik-server --since 10m --no-task-ids 2>&1 | tail -40"

# Check worker for job queue connectivity
ssh chester@10.0.0.211 \
  "docker service logs authentik_authentik-worker --since 10m --no-task-ids 2>&1 | tail -40"
```

- [ ] No `FATAL` or `ERROR` messages relating to database connection in server logs.
- [ ] No `FATAL` or `ERROR` messages relating to Redis connection in server or worker logs.
- [ ] Database migration messages complete without errors.
- [ ] No repeated container restart events (no `started 2+ times`).

### 4.5 Resource limits in effect

| Service | Memory limit | CPU limit |
| :--- | :---: | :---: |
| `authentik-postgres` | 1 G | 0.75 |
| `authentik-redis` | 512 M | 0.50 |
| `authentik-server` | 2 G | 1.0 |
| `authentik-worker` | 1 G | 0.75 |

```bash
ssh chester@10.0.0.211 \
  "docker service inspect authentik_authentik-server \
   --format '{{.Spec.TaskTemplate.Resources.Limits.MemoryBytes}}'"
# Expected: 2147483648 (2 GB)
```

- [ ] Resource limits are present and match the table above.

---

## Phase 5 — Ingress and functional verification

### 5.1 Traefik route registration

Traefik routes are published via `traefik-kop`. Verify the route is active before
testing the public endpoint.

```bash
# Check Traefik router for the authentik rule
curl -fsS http://10.0.0.151:8080/api/http/routers/authentik@docker \
  | python3 -m json.tool | grep -E '"rule"|"status"'
# Expected: "rule": "Host(...sso.castaldifamily.com...)", "status": "enabled"
```

- [ ] Traefik router `authentik@docker` exists and is `enabled`.
- [ ] Router rule matches `Host('sso.castaldifamily.com')`.
- [ ] Middlewares include `security-headers@file` and `ratelimit-basic@file`.

### 5.2 HTTPS endpoint reachability

```bash
# TLS handshake and HTTP 200/302 response
curl -fsS -o /dev/null -w "%{http_code} %{ssl_verify_result}" \
  https://sso.castaldifamily.com
# Expected: 200 0  (or 302 0 for a redirect to login)
```

- [ ] curl returns HTTP `200` or `302`.
- [ ] `ssl_verify_result` is `0` (certificate valid).
- [ ] Response is not a Traefik 404 or 502.

### 5.3 Login page load

Open `https://sso.castaldifamily.com` in a browser.

- [ ] Authentik login page loads without JavaScript errors.
- [ ] Page title includes "authentik" or "Sign in".
- [ ] No TLS certificate warning from the browser.

### 5.4 Admin UI readiness (if initial deploy)

Navigate to `https://sso.castaldifamily.com/if/flow/initial-setup/`

- [ ] Initial setup flow is reachable on first-run bootstrap.
- [ ] Skip this step if the instance already existed; do not re-run initial setup
      on an existing install.

---

## Phase 6 — Post-deploy handoff

### 6.1 Monitoring integration

Authentik is referenced as the SSO provider in `group_vars/all.yml`:

```yaml
monitoring:
  authentik_host: "https://sso.castaldifamily.com"
```

- [ ] Uptime Kuma has a monitor for `https://sso.castaldifamily.com`.
- [ ] Prometheus or health check system is alerting on `authentik_authentik-server`
      replica count dropping below 1.

### 6.2 Backup verification

- [ ] `/mnt/homelab/apps/authentik/data/database` is included in backup scope.
- [ ] A manual backup snapshot was taken before or immediately after deploy.
- [ ] Restore procedure is documented and tested (or explicitly deferred).

### 6.3 Secret rotation awareness

| Secret | Rotation procedure |
| :--- | :--- |
| `vault_authentik_secret_key` | Update vault → redeploy stack → running sessions are invalidated |
| `vault_authentik_postgres_password` | Update vault AND postgres user password → redeploy |

- [ ] Rotation procedure is known to the deployment owner.

### 6.4 Evidence capture

```bash
# Save service state snapshot
ssh chester@10.0.0.211 \
  "docker service ls --filter label=com.docker.stack.namespace=authentik" \
  > ../outputs/authentik_service_snapshot_$(date +%Y%m%dT%H%M%S).txt
```

- [ ] Deploy log saved to `outputs/authentik_deploy_<timestamp>.log`.
- [ ] Service state snapshot saved to `outputs/authentik_service_snapshot_<timestamp>.txt`.
- [ ] Deployment timestamp and verification timestamp recorded in this checklist.

### 6.5 Deployment sign-off

| Field | Value |
| :--- | :--- |
| Deployment owner | |
| Deployment timestamp | |
| Verification timestamp | |
| Endpoint verified | `https://sso.castaldifamily.com` |
| Final status | ☐ GREEN — all phases passed |

---

## Rollback procedure

If deployment fails or causes instability, remove the stack and preserve data.

```bash
cd /home/chester/homelab/ansible

ansible-playbook \
  -i inventory/hosts.ini \
  playbooks/docker/deploy_authentik.yml \
  -e "authentik_deploy_state=absent" \
  --vault-password-file .vault_pass
```

> [!WARNING]
> `authentik_deploy_state=absent` removes the **Swarm stack** (containers,
> services, configs) but does **not** delete the bind-mount data directories.
> Data at `/mnt/homelab/apps/authentik` is preserved for re-deploy or restore.

- [ ] Stack removed cleanly (`docker stack ls` shows no `authentik` entry).
- [ ] Data directories still intact on `swarm-manager-1`.
- [ ] Root cause identified before re-deploying.

---

## Troubleshooting matrix

### Validation assert fails: secrets not defined or placeholder

**Symptom:** Playbook fails on `Assert vault_authentik_secret_key is defined` or
`Assert Authentik secrets are not placeholders`.

**Check:**

```bash
ansible -i inventory/hosts.ini localhost \
  -m ansible.builtin.debug \
  -a "var=vault_authentik_secret_key" \
  -e "@group_vars/all.yml" \
  --vault-password-file .vault_pass
```

**Fix:** Encrypt and store the correct value:

```bash
ansible-vault encrypt_string 'YOUR-KEY' \
  --name 'vault_authentik_secret_key' \
  --vault-password-file .vault_pass
# Paste output into group_vars/vault/all.yml
```

---

### Validation assert fails: data paths missing

**Symptom:** Playbook fails on `Assert required Authentik paths exist before deploy`.

**Check:**

```bash
ssh chester@10.0.0.211 "ls -la /mnt/homelab/apps/authentik/"
```

**Fix (fresh install only):**

```bash
ssh chester@10.0.0.211 "sudo mkdir -p \
  /mnt/homelab/apps/authentik/data/{database,redis,media,config,blueprints}"
```

**Fix (existing install):** Restore from backup before creating directories.

---

### Swarm assert fails: manager not active or not control plane

**Symptom:** Playbook fails on `Assert target is an active Swarm manager`.

**Check:**

```bash
ssh chester@10.0.0.211 "docker info --format '{{.Swarm.LocalNodeState}}'"
```

**Fix:** Investigate Swarm manager health. Do not proceed until a healthy quorum
manager is the deploy target.

---

### Services not converging to 1/1

**Symptom:** `docker service ls` shows `0/1` or a service cycles through restarts.

**Check:**

```bash
ssh chester@10.0.0.211 \
  "docker service ps authentik_authentik-server --no-trunc"
```

Look for failure reasons in the `Error` column.

**Common causes:**

| Cause | Evidence in logs | Fix |
| :--- | :--- | :--- |
| Secret key mismatch | `cryptography error` or `key invalid` in server logs | Re-check vault value, redeploy |
| Postgres not healthy yet | `connection refused` in server logs | Wait for postgres `(healthy)`, then check server |
| Redis not reachable | `redis connection error` in server or worker logs | Confirm `authentik-redis` is `1/1` healthy first |
| Missing bind-mount path | `no such file or directory` in container start | Create path, redeploy |
| Insufficient memory | OOM kill in `docker service ps` error column | Check node resources, adjust limits if needed |

---

### Traefik route not registered or 502 response

**Symptom:** `curl https://sso.castaldifamily.com` returns `502 Bad Gateway` or
connection refused.

**Check:**

```bash
# Confirm traefik-kop is running (Swarm stack)
ssh chester@10.0.0.211 \
  "docker service ls --filter name=traefik-kop"

# Check server is listening on port 9000
ssh chester@10.0.0.211 \
  "docker service ps authentik_authentik-server --filter desired-state=running"
```

**Common causes:**

- `traefik-kop` is not running → deploy monitoring stack first.
- `authentik-server` is not bound on port `9000` → check replica and restart.
- `edge_routing.swarm.bind_ip` is incorrect in `group_vars/all.yml` → verify
  it resolves to an active Swarm node.
- Cloudflare DNS is not pointing to `10.0.0.151` → verify DNS record for
  `sso.castaldifamily.com`.

---

### Database migration errors on first boot

**Symptom:** Server logs show migration errors or `relation does not exist`.

**Check:**

```bash
ssh chester@10.0.0.211 \
  "docker service logs authentik_authentik-server --since 5m 2>&1 | grep -i 'migrat\|error\|fatal'"
```

**Fix:** Migrations run automatically on startup. If they fail:

1. Check postgres is `(healthy)` and accepting connections.
2. Check `vault_authentik_postgres_password` in vault matches the running
   postgres password.
3. Restart the server service to trigger a re-run:

```bash
ssh chester@10.0.0.211 \
  "docker service update --force authentik_authentik-server"
```

---

## Reference

| Resource | Location |
| :--- | :--- |
| Deploy playbook | `ansible/playbooks/docker/deploy_authentik.yml` |
| Stack template | `ansible/templates/stacks/authentik.stack.yml` |
| Shared variables | `ansible/group_vars/all.yml` |
| Vault secrets | `ansible/group_vars/vault/all.yml` |
| Authentik docs | <https://goauthentik.io/docs> |
| Authentik changelog | <https://github.com/goauthentik/authentik/releases> |
| Swarm cluster baseline | `outputs/swarm_audit_20260314T122134.md` |