# Headscale - Self-Hosted Tailscale Control Server

**Status**: 🟢 Live  
**Host**: Calypso (`100.103.48.78`)  
**Stack File**: `hosts/synology/calypso/headscale.yaml`  
**Public URL**: `https://headscale.vish.gg:8443`  
**Admin UI**: `https://headscale.vish.gg:8443/admin` (Headplane, Authentik SSO)  
**Ports**: 8085 (API), 3002 (Headplane UI), 9099 (Metrics), 50443 (gRPC)

---

## Overview

[Headscale](https://headscale.net/) is an open-source, self-hosted implementation of the Tailscale control server. It allows you to run your own Tailscale coordination server, giving you full control over your mesh VPN network.

### Why Self-Host?

| Feature | Tailscale Cloud | Headscale |
|---------|-----------------|-----------|
| **Control** | Tailscale manages | You manage |
| **Data Privacy** | Keys on their servers | Keys on your servers |
| **Cost** | Free tier limits | Unlimited devices |
| **OIDC Auth** | Limited | Full control |
| **Network Isolation** | Shared infra | Your infra only |

---

## Recommended Host: Calypso

### Why Calypso?

| Factor | Rationale |
|--------|-----------|
| **Authentik Integration** | OIDC provider already running for SSO |
| **Nginx Proxy Manager** | HTTPS/SSL termination already configured |
| **Infrastructure Role** | Hosts auth, git, networking services |
| **Stability** | Synology NAS = 24/7 uptime |
| **Resources** | Low footprint fits alongside 52 containers |

### Alternative Hosts

- **Homelab VM**: Viable, but separates auth from control plane
- **Concord NUC**: Running Home Assistant, keep it focused
- **Atlantis**: Primary media server, avoid network-critical services

---

## Architecture

```
                         Internet
                             │
                             ▼
                   ┌─────────────────┐
                   │  NPM (Calypso)  │  ← SSL termination
                   │ headscale.vish.gg
                   └────────┬────────┘
                            │ :8085
                            ▼
                   ┌─────────────────┐
                   │   Headscale     │  ← Control plane
                   │   (container)   │
                   └────────┬────────┘
                            │ OIDC
                            ▼
                   ┌─────────────────┐
                   │   Authentik     │  ← User auth
                   │  sso.vish.gg    │
                   └─────────────────┘
```

### Network Flow

1. Tailscale clients connect to `headscale.vish.gg` (HTTPS)
2. NPM terminates SSL, forwards to Headscale container
3. Users authenticate via Authentik OIDC
4. Headscale coordinates the mesh network
5. Direct connections established between peers (via DERP relays if needed)

---

## Services

| Service | Container | Port | Purpose |
|---------|-----------|------|---------|
| Headscale | `headscale` | 8085→8080 | Control server API |
| Headscale | `headscale` | 50443 | gRPC API |
| Headscale | `headscale` | 9099→9090 | Prometheus metrics |
| Headplane | `headplane` | 3002→3000 | Web admin UI (replaces headscale-ui) |

---

## Pre-Deployment Setup

### Step 1: Create Authentik Application

In Authentik at `https://sso.vish.gg`:

#### 1.1 Create OAuth2/OIDC Provider

1. Go to **Applications** → **Providers** → **Create**
2. Select **OAuth2/OpenID Provider**
3. Configure:

| Setting | Value |
|---------|-------|
| Name | `Headscale` |
| Authorization flow | `default-provider-authorization-implicit-consent` |
| Client type | `Confidential` |
| Client ID | (auto-generated, copy this) |
| Client Secret | (auto-generated, copy this) |
| Redirect URIs | `https://headscale.vish.gg/oidc/callback` |
| Signing Key | `authentik Self-signed Certificate` |

4. Under **Advanced protocol settings**:
   - Scopes: `openid`, `profile`, `email`
   - Subject mode: `Based on the User's Email`

#### 1.2 Create Application

1. Go to **Applications** → **Applications** → **Create**
2. Configure:

| Setting | Value |
|---------|-------|
| Name | `Headscale` |
| Slug | `headscale` |
| Provider | Select the provider you created |
| Launch URL | `https://headscale.vish.gg` |

#### 1.3 Copy Credentials

Save these values to update the stack:
- **Client ID**: `xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx`
- **Client Secret**: `xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx`

### Step 2: Configure NPM Proxy Hosts

In Nginx Proxy Manager at `http://calypso.vish.local:81`:

#### 2.1 Headscale API Proxy

| Setting | Value |
|---------|-------|
| Domain Names | `headscale.vish.gg` |
| Scheme | `http` |
| Forward Hostname/IP | `headscale` |
| Forward Port | `8080` |
| Block Common Exploits | ✅ |
| Websockets Support | ✅ |

**SSL Tab:**
- SSL Certificate: Request new Let's Encrypt
- Force SSL: ✅
- HTTP/2 Support: ✅

#### 2.2 Headplane UI Proxy (via /admin path on main domain)

The Headplane UI is served at `https://headscale.vish.gg:8443/admin` via NPM path routing.

| Setting | Value |
|---------|-------|
| Domain Names | `headscale.vish.gg` |
| Scheme | `http` |
| Forward Hostname/IP | `headplane` |
| Forward Port | `3000` |
| Custom Location | `/admin` |

### Step 3: Verify Authentik Network

```bash
# SSH to Calypso and check the network name
ssh admin@calypso.vish.local
docker network ls | grep authentik
```

If the network name differs from `authentik-net`, update the stack file.

### Step 4: Update Stack Configuration

Edit `hosts/synology/calypso/headscale.yaml`:

```yaml
oidc:
  client_id: "REDACTED_CLIENT_ID"
  client_secret: "REDACTED_CLIENT_SECRET"
```

---

## Deployment

### Option A: GitOps via Portainer

```bash
# 1. Commit the stack file
cd /path/to/homelab
git add hosts/synology/calypso/headscale.yaml
git commit -m "feat(headscale): Add self-hosted Tailscale control server"
git push origin main

# 2. Create GitOps stack via API
curl -X POST \
  -H "X-API-Key: "REDACTED_API_KEY" \
  -H "Content-Type: application/json" \
  "http://vishinator.synology.me:10000/api/stacks/create/standalone/repository?endpointId=443397" \
  -d '{
    "name": "headscale-stack",
    "repositoryURL": "https://git.vish.gg/Vish/homelab.git",
    "repositoryReferenceName": "refs/heads/main",
    "composeFile": "hosts/synology/calypso/headscale.yaml",
    "repositoryAuthentication": true,
    "repositoryUsername": "",
    "repositoryPassword": "YOUR_GIT_TOKEN",
    "autoUpdate": {
      "interval": "5m",
      "forceUpdate": false,
      "forcePullImage": false
    }
  }'
```

### Option B: Manual via Portainer UI

1. Go to Portainer → Stacks → Add stack
2. Select "Repository"
3. Configure:
   - Repository URL: `https://git.vish.gg/Vish/homelab.git`
   - Reference: `refs/heads/main`
   - Compose path: `hosts/synology/calypso/headscale.yaml`
   - Authentication: Enable, enter Git token
4. Enable GitOps updates with 5m polling
5. Deploy

---

## Post-Deployment Verification

### 1. Check Container Health

```bash
# Via Portainer API
curl -s -H "X-API-Key: TOKEN" \
  "http://vishinator.synology.me:10000/api/endpoints/443397/docker/containers/json" | \
  jq '.[] | select(.Names[0] | contains("headscale")) | {name: .Names[0], state: .State}'
```

### 2. Test API Endpoint

```bash
curl -s https://headscale.vish.gg/health
# Should return: {"status":"pass"}
```

### 3. Check Metrics

```bash
curl -s http://calypso.vish.local:9099/metrics | head -20
```

---

## Client Setup

### Linux/macOS

```bash
# Install Tailscale client
curl -fsSL https://tailscale.com/install.sh | sh

# Connect to your Headscale server
sudo tailscale up --login-server=https://headscale.vish.gg

# This will open a browser for OIDC authentication
# After auth, the device will be registered
```

### With Pre-Auth Key

```bash
# Generate key in Headscale first (see Admin Commands below)
sudo tailscale up --login-server=https://headscale.vish.gg --authkey=YOUR_PREAUTH_KEY
```

### iOS/Android

1. Install Tailscale app from App Store/Play Store
2. Open app → Use a different server
3. Enter: `https://headscale.vish.gg`
4. Authenticate via Authentik

### Verify Connection

```bash
tailscale status
# Should show your device and any other connected peers

tailscale ip
# Shows your Tailscale IP (100.64.x.x)
```

---

## Admin Commands

Execute commands inside the Headscale container on Calypso:

```bash
# SSH to Calypso
ssh -p 62000 Vish@100.103.48.78

# Enter container (full path required on Synology)
sudo /usr/local/bin/docker exec headscale headscale <command>
```

> **Note**: Headscale v0.28+ uses numeric user IDs. Get the ID with `users list` first, then pass `--user <ID>` to other commands.

### User Management

```bash
# List users (shows numeric IDs)
headscale users list

# Create a user
headscale users create myuser

# Rename a user
headscale users rename --identifier <id> <newname>

# Delete a user
headscale users destroy --identifier <id>
```

### Node Management

```bash
# List all nodes
headscale nodes list

# Register a node manually
headscale nodes register --user <user-id> --key nodekey:xxxxx

# Delete a node
headscale nodes delete --identifier <node-id>

# Expire a node (force re-auth)
headscale nodes expire --identifier <node-id>

# Move node to different user
headscale nodes move --identifier <node-id> --user <user-id>
```

### Pre-Auth Keys

```bash
# Create a pre-auth key (single use)
headscale preauthkeys create --user <user-id>

# Create reusable key (expires in 24h)
headscale preauthkeys create --user <user-id> --reusable --expiration 24h

# List keys
headscale preauthkeys list --user <user-id>
```

### API Keys

```bash
# Create API key for external integrations
headscale apikeys create --expiration 90d

# List API keys
headscale apikeys list
```

---

## Route & Exit Node Management

> **How it works**: Exit node and subnet routes are a two-step process.
> 1. The **node** must advertise the route via `tailscale set --advertise-exit-node` or `--advertise-routes`.
> 2. The **server** (Headscale) must approve the advertised route. Without approval, the route is visible but not active.

All commands below are run inside the Headscale container on Calypso:

```bash
ssh -p 62000 Vish@100.103.48.78 "sudo /usr/local/bin/docker exec headscale headscale <command>"
```

### List All Routes

Shows every node that is advertising routes, what is approved, and what is actively serving:

```bash
headscale nodes list-routes
```

Output columns:
- **Approved**: routes the server has approved
- **Available**: routes the node is currently advertising
- **Serving (Primary)**: routes actively being used

### Approve an Exit Node

After a node runs `tailscale set --advertise-exit-node`, approve it server-side:

```bash
# Find the node ID first
headscale nodes list

# Approve exit node routes (IPv4 + IPv6)
headscale nodes approve-routes --identifier <node-id> --routes '0.0.0.0/0,::/0'
```

If the node also advertises a subnet route you want to keep approved alongside exit node:

```bash
# Example: calypso also advertises 192.168.0.0/24
headscale nodes approve-routes --identifier 12 --routes '0.0.0.0/0,::/0,192.168.0.0/24'
```

> **Important**: `approve-routes` **replaces** the full approved route list for that node. Always include all routes you want active (subnet routes + exit routes) in a single command.

### Approve a Subnet Route Only

For nodes that advertise a local subnet (e.g. a router or NAS providing LAN access) but are not exit nodes:

```bash
# Example: approve 192.168.0.0/24 for atlantis
headscale nodes approve-routes --identifier 11 --routes '192.168.0.0/24'
```

### Revoke / Remove Routes

To remove approval for a route, re-run `approve-routes` omitting that route:

```bash
# Example: remove exit node approval from a node, keep subnet only
headscale nodes approve-routes --identifier <node-id> --routes '192.168.0.0/24'

# Remove all approved routes from a node
headscale nodes approve-routes --identifier <node-id> --routes ''
```

### Current Exit Nodes (April 2026)

The following nodes are approved as exit nodes:

| Node | ID | Exit Node Routes | Subnet Routes |
|------|----|-----------------|---------------|
| vish-concord-nuc | 5 | `0.0.0.0/0`, `::/0` | `192.168.68.0/22` |
| setillo | 6 | `0.0.0.0/0`, `::/0` | `192.168.69.0/24` |
| truenas-scale | 8 | `0.0.0.0/0`, `::/0` | — |
| atlantis | 11 | `0.0.0.0/0`, `::/0` | — |
| calypso | 12 | `0.0.0.0/0`, `::/0` | `192.168.0.0/24` |
| gl-mt3000 | 16 | `0.0.0.0/0`, `::/0` | — (exit-node only as of 2026-04-18) |
| gl-be3600 | 17 | `0.0.0.0/0`, `::/0` | — (exit-node only as of 2026-04-18) |
| homeassistant | 19 | `0.0.0.0/0`, `::/0` | — |

---

## Adding a New Node

### Step 1: Install Tailscale on the new device

**Linux:**
```bash
curl -fsSL https://tailscale.com/install.sh | sh
```

**Synology NAS:** Install the Tailscale package from Package Center (or manually via `.spk`).

**TrueNAS Scale:** Available as an app in the TrueNAS app catalog.

**Home Assistant:** Install via the HA Add-on Store (search "Tailscale").

**OpenWrt / GL.iNet routers:** Install `tailscale` via `opkg` or the GL.iNet admin panel.

### Step 2: Generate a pre-auth key (recommended for non-interactive installs)

```bash
# Get the user ID first
headscale users list

# Create a reusable pre-auth key (24h expiry)
headscale preauthkeys create --user <user-id> --reusable --expiration 24h
```

### Step 3: Connect the node

**Interactive (browser-based OIDC auth):**
```bash
sudo tailscale up --login-server=https://headscale.vish.gg
# Follow the printed URL to authenticate via Authentik
```

**Non-interactive (pre-auth key):**
```bash
sudo tailscale up --login-server=https://headscale.vish.gg --authkey=<preauth-key>
```

**With exit node advertising enabled from the start:**
```bash
sudo tailscale up \
  --login-server=https://headscale.vish.gg \
  --authkey=<preauth-key> \
  --advertise-exit-node
```

**With subnet route advertising:**
```bash
sudo tailscale up \
  --login-server=https://headscale.vish.gg \
  --authkey=<preauth-key> \
  --advertise-routes=192.168.1.0/24
```

### Step 4: Verify the node registered

```bash
headscale nodes list
# New node should appear with an assigned 100.x.x.x IP
```

### Step 5: Approve routes (if needed)

If the node advertised exit node or subnet routes:
```bash
headscale nodes list-routes
# Find the node ID and approve as needed
headscale nodes approve-routes --identifier <node-id> --routes '0.0.0.0/0,::/0'
```

### Step 6: (Optional) Rename the node

Headscale uses the system hostname by default. To rename:
```bash
headscale nodes rename --identifier <node-id> <new-name>
```

---

## Configuration Reference

### Key Settings in `config.yaml`

| Setting | Value | Description |
|---------|-------|-------------|
| `server_url` | `https://headscale.vish.gg:8443` | Public URL for clients (port 8443 required) |
| `listen_addr` | `0.0.0.0:8080` | Internal listen address |
| `prefixes.v4` | `100.64.0.0/10` | IPv4 CGNAT range |
| `prefixes.v6` | `fd7a:115c:a1e0::/48` | IPv6 ULA range |
| `dns.magic_dns` | `true` | Enable MagicDNS |
| `dns.base_domain` | `tail.vish.gg` | DNS suffix for devices |
| `database.type` | `sqlite` | Database backend |
| `oidc.issuer` | `https://sso.vish.gg/...` | Authentik OIDC endpoint |

### DERP Configuration

Using Tailscale's public DERP servers (recommended):
```yaml
derp:
  urls:
    - https://controlplane.tailscale.com/derpmap/default
  auto_update_enabled: true
```

For self-hosted DERP, see: https://tailscale.com/kb/1118/custom-derp-servers

---

## Monitoring Integration

### Prometheus Scrape Config

Add to your Prometheus configuration:

```yaml
scrape_configs:
  - job_name: 'headscale'
    static_configs:
      - targets: ['calypso.vish.local:9099']
        labels:
          instance: 'headscale'
```

### Key Metrics

| Metric | Description |
|--------|-------------|
| `headscale_connected_peers` | Number of connected peers |
| `headscale_registered_machines` | Total registered machines |
| `headscale_online_machines` | Currently online machines |

---

## Troubleshooting

### Client Can't Connect

1. **Check DNS resolution**: `nslookup headscale.vish.gg`
2. **Check SSL certificate**: `curl -v https://headscale.vish.gg/health`
3. **Check NPM logs**: Portainer → Calypso → nginx-proxy-manager → Logs
4. **Check Headscale logs**: `docker logs headscale`

### OIDC Authentication Fails

1. **Verify Authentik is reachable**: `curl https://sso.vish.gg/.well-known/openid-configuration`
2. **Check redirect URI**: Must exactly match in Authentik provider
3. **Check client credentials**: Ensure ID/secret are correct in config
4. **Check Headscale logs**: `docker logs headscale | grep oidc`

### Nodes Not Connecting to Each Other

1. **Check DERP connectivity**: Nodes may be relaying through DERP
2. **Check firewall**: Ensure UDP 41641 is open for direct connections
3. **Check node status**: `tailscale status` on each node

### Synology NAS: Userspace Networking Limitation

Synology Tailscale runs in **userspace networking mode** (`NetfilterMode: 0`) by default. This means:

- No `tailscale0` tun device is created
- No kernel routing table 52 entries exist
- `tailscale ping` works (uses the daemon directly), but **TCP traffic to Tailscale IPs fails**
- Other services on the NAS cannot reach Tailscale IPs of remote peers

**Workaround**: Use LAN IPs instead of Tailscale IPs for service-to-service communication when both hosts are on the same network. This is why all Atlantis arr services use `192.168.0.210` (homelab-vm LAN IP) for Signal notifications instead of `100.67.40.126` (Tailscale IP).

**Why not `tailscale configure-host`?** Running `tailscale configure-host` + restarting the Tailscale service temporarily enables kernel networking, but tailscaled becomes unstable and crashes repeatedly (every few minutes). The boot-up DSM task "Tailscale enable outbound" runs `configure-host` on boot, but the effect does not persist reliably. This is a known limitation of the Synology Tailscale package.

**SSL certificate gotcha**: When connecting from Synology to `headscale.vish.gg`, split-horizon DNS resolves to Calypso's LAN IP (192.168.0.250). Port 443 there serves the **Synology default certificate** (CN=synology), not the headscale cert. Use `https://headscale.vish.gg:8443` as the login-server URL — port 8443 serves the correct headscale certificate.

```bash
# Check if Tailscale is in userspace mode on a Synology NAS
tailscale debug prefs | grep NetfilterMode
# NetfilterMode: 0  = userspace (no tun device, no TCP routing)
# NetfilterMode: 1  = kernel (tun device + routing, but unstable on Synology)

# Check if tailscale0 exists
ip link show tailscale0
```

### Container Won't Start

1. **Check config syntax**: YAML formatting errors
2. **Check network exists**: `docker network ls | grep authentik`
3. **Check volume permissions**: Synology may have permission issues

---

## Backup

### Data to Backup

| Path | Content |
|------|---------|
| `headscale-data:/var/lib/headscale/db.sqlite` | User/node database |
| `headscale-data:/var/lib/headscale/private.key` | Server private key |
| `headscale-data:/var/lib/headscale/noise_private.key` | Noise protocol key |

### Backup Command

```bash
# On Calypso
docker run --rm -v headscale-data:/data -v /volume1/backups:/backup \
  alpine tar czf /backup/headscale-backup-$(date +%Y%m%d).tar.gz /data
```

---

## Migration from Tailscale

If migrating existing devices from Tailscale cloud:

1. **On each device**: `sudo tailscale logout`
2. **Connect to Headscale**: `sudo tailscale up --login-server=https://headscale.vish.gg`
3. **Re-establish routes**: Configure exit nodes and subnet routes as needed

**Note**: You cannot migrate Tailscale cloud configuration directly. ACLs, routes, and settings must be reconfigured.

---

## Related Documentation

- [Authentik SSO Setup](authentik.md)
- [Nginx Proxy Manager](nginx-proxy-manager.md)
- [GitOps Guide](../../admin/gitops.md)
- [Monitoring Setup](../../admin/monitoring.md)

---

## External Resources

- [Headscale Documentation](https://headscale.net/stable/)
- [Headscale GitHub](https://github.com/juanfont/headscale)
- [Headplane GitHub](https://github.com/tale/headplane) (Admin UI — replaces headscale-ui)
- [Tailscale Client Docs](https://tailscale.com/kb/)

---

*Last updated: 2026-03-29 (documented Synology userspace networking limitation and SSL cert gotcha; switched Signal notifications to LAN IP)*