| name | tailscale |
| description | Deploy and manage the self-hosted Tailscale/Headscale ecosystem: a Headscale control server, tailscale clients, ACL policies, node lifecycle, subnet routing, DERP relays, and backup/migration. Use when the user mentions Tailscale, Headscale, tailnet, mesh VPN, WireGuard mesh, or self-hosted VPN infrastructure. |
| license | MIT |
| compatibility | Requires bash, Python 3.8+, jq, curl, and access to a Headscale server or the `headscale` CLI. Tailscale client (`tailscale`) must be installed on target machines. |
| metadata | {"tags":"tailscale, headscale, vpn, wireguard, mesh, networking, homelab","spec-version":"1.0"} |
Tailscale + Headscale Skill Bundle
This umbrella skill covers the self-hosted Tailscale ecosystem using Headscale
as the open-source control server. It provides 7 sub-skills that are auto-loaded by context.
Auto-Loading by Context
When the user's message matches a trigger keyword, the corresponding sub-skill's SKILL.md
is loaded. Multiple sub-skills can load together when triggers overlap.
| Trigger Keywords | Sub-Skill(s) Loaded |
|---|
| "deploy headscale", "install headscale", "setup headscale server", "headscale config" | headscale-deploy |
| "ACL", "policy file", "tailnet policy", "access control", "grant", "tag owners" | tailnet-policy |
| "install tailscale", "connect to headscale", "tailscale client", "tailscale up", "tailscale status", "diagnose tailscale", "connectivity" | tailscale-client |
| "auth key", "preauthkey", "register node", "approve node", "tag node", "node list", "decommission node" | headscale-node-lifecycle |
| "subnet router", "exit node", "advertise route", "approve route" | headscale-routing |
| "DERP", "relay", "peer relay", "STUN" | headscale-derp |
| "backup headscale", "restore headscale", "migrate headscale", "headscale backup" | headscale-backup |
| "Tailscale", "Headscale", "tailnet", "mesh VPN", "WireGuard mesh", "self-hosted VPN" | Loads this umbrella SKILL.md for navigation |
Sub-Skill Ordering & Dependencies
headscale-deploy ─────┬──> tailnet-policy ───> headscale-routing
│
├──> headscale-node-lifecycle
│
├──> tailscale-client
│
├──> headscale-derp
│
└──> headscale-backup (prerequisite: a running headscale instance)
- headscale-deploy must be completed first — the others require a running Headscale server
- tailnet-policy (configures ACLs) is recommended before opening the tailnet to other users
- headscale-derp is optional but recommended for reliability across NATs
- headscale-backup should be run regularly on any production deployment
Root Scripts (Shared Utilities)
These live in scripts/ at the bundle root and are available to all sub-skills.
Available Scripts
| Script | Purpose | Invocation |
|---|
scripts/headscale-health-check.sh | Probe Headscale server health: version, node count, and DB integrity. Run it after any control-server change and as the first diagnostic when nodes or clients misbehave. | scripts/headscale-health-check.sh --json |
scripts/headscale-backup.sh | Full backup of the Headscale server (sqlite + config + policy + certs) to a restorable archive. Run it on a schedule for any production deployment and before upgrades or migrations; --dry-run previews without writing. | scripts/headscale-backup.sh --dry-run |
scripts/headscale-restore.sh | Restore a Headscale server from a backup archive. Run it during disaster recovery or migration onto a fresh host; always verify node list and policy afterwards. | scripts/headscale-restore.sh --backup headscale-backup-2026-01-01.tar.gz |
scripts/tailscale-status-json.sh | Structured wrapper around tailscale status --json with peer diagnostics. Run it from any client to check connectivity, peers, and relay/direct paths in machine-readable form. | scripts/tailscale-status-json.sh |
scripts/test-all.sh | Smoke test across all bundle scripts (--help, syntax, executability) without requiring a running Headscale. Run it after modifying any bundled script; CI runs it via scripts/check-skill-tests.py. | bash scripts/test-all.sh |
Templates
Templates live in templates/ and cover common deployment patterns:
templates/docker-compose-headscale.yaml — Headscale + embedded DERP + Traefik TLStemplates/headscale-config.yaml — Annotated full headscale configurationtemplates/policy-allow-all.json — Minimal allow-all policytemplates/policy-deny-all.json — Locked-down deny-all policytemplates/policy-tagged-segmented.json — Tag-based access modeltemplates/derp-map.json — Custom DERP relay map
Environment Variables
| Variable | Used By | Purpose |
|---|
HEADSCALE_URL | All | Headscale server URL (e.g. https://headscale.example.com) |
HEADSCALE_API_KEY | All | Headscale API key (created via headscale apikeys create) |
TAILSCALE_AUTHKEY | tailscale-client | Pre-authenticated key for non-interactive client setup |
Use the CLI tools
All scripts use --json, --dry-run, and have informative --help output.
Scripts relative to bundle root: scripts/<tool> or skills/<sub-skill>/scripts/<tool>.
See the individual sub-skill SKILL.md for detailed usage.
Prerequisites
- bash, Python 3.8+,
jq, and curl on the host running the scripts (per compatibility).
- A running Headscale server with
HEADSCALE_URL and HEADSCALE_API_KEY set for server-side operations (API key created via headscale apikeys create); TAILSCALE_AUTHKEY for non-interactive client enrollment.
- The
tailscale client installed on target machines for status and routing sub-skills; the headscale CLI (or API access) for control-server administration.
- For headscale-backup/restore: filesystem access to the server's sqlite DB, config, policy, and cert paths, plus storage for archives off the control-server host.
Limitations
- This bundle assumes a self-hosted Headscale control plane — it does not manage Tailscale's hosted SaaS (see When not to use).
- Scripts check environment variables at runtime and error helpfully when missing; they do not create credentials themselves.
- Backup/restore operates on the files present on the control-server host; it cannot recover data that was never backed up, and a restore should always be followed by health verification.
- Sub-skill scripts live under
skills/<sub-skill>/scripts/ and are documented in their own SKILL.md files, not here.
When not to use
Do not load this umbrella when a task maps to a single sub-skill — load the matching sub-skill directly (e.g. headscale-deploy, tailnet-policy, tailscale-client). It assumes a self-hosted Headscale control server; for Tailscale's hosted SaaS control plane, or for non-Tailscale VPN tooling, use the appropriate network skill instead.
