tailscale

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 TLS
• templates/headscale-config.yaml — Annotated full headscale configuration
• templates/policy-allow-all.json — Minimal allow-all policy
• templates/policy-deny-all.json — Locked-down deny-all policy
• templates/policy-tagged-segmented.json — Tag-based access model
• templates/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.