Rework the description frontmatter of 4 moved skills (tailscale, and workflow-architect sub-skills bundle-builder, interviewer, observer) so each starts with a recognized imperative verb, and add "## When not to use" body sections to all 13 moved skills surfaced by the flatten move (research-and-vault, tailscale + its 7 sub-skills, workflow-architect + its 3 sub-skills) so every one defines a negative boundary. Trigger vocabulary is preserved and every description stays under 1024 chars. Regenerate llms.txt and .claude-plugin/marketplace.json, which embed the tailscale description. Co-authored-by: factory-droid[bot] <138933559+factory-droid[bot]@users.noreply.github.com>
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name, description, license, compatibility, metadata
| name | description | license | compatibility | metadata | ||||
|---|---|---|---|---|---|---|---|---|
| tailscale | 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. | MIT | 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. |
|
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:
scripts/headscale-health-check.sh— Probe Headscale server version, node count, DB integrityscripts/headscale-backup.sh— Full backup (sqlite + config + policy + certs)scripts/headscale-restore.sh— Restore from backup archivescripts/tailscale-status-json.sh— Structuredtailscale status --jsonwrapperscripts/test-all.sh— Smoke test across all sub-skills
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.
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.