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Tailscale / Headscale — Self-Hosted Mesh VPN Bundle
A comprehensive bundle of 7 sub-skills covering the entire self-hosted Tailscale ecosystem using Headscale as the open-source control server. Deploy, configure, and maintain your own WireGuard-based mesh VPN.
Why Install This Bundle
When your agent loads this bundle, it becomes a Tailscale/Headscale infrastructure engineer who can handle the full lifecycle:
- Deploy Headscale — install and configure the control server
- Author tailnet policies — ACL rules, tag-based access control, user groups
- Manage node lifecycle — auth keys, registration, tagging, decommissioning
- Configure clients — install and connect Tailscale to your Headscale server
- Set up routing — subnet routers and exit nodes
- Deploy DERP relays — reliable peer-to-peer connectivity across NATs
- Backup and migrate — regular backup and restoration of the control server
What You Get
| Directory | Purpose |
|---|---|
SKILL.md |
Bundle umbrella — trigger-based auto-loading for 7 sub-skills |
skills/ |
7 sub-skills: headscale-deploy, tailnet-policy, headscale-node-lifecycle, tailscale-client, headscale-routing, headscale-derp, headscale-backup |
scripts/ |
23 shared scripts with --json and --dry-run support |
references/ |
8 reference documents |
templates/ |
6 templates for policy files and configs |
Quick Start
- Deploy Headscale first — install the control server
- Configure tailnet policy — set up ACLs before opening to users
- Manage nodes — register and tag machines on your tailnet
- Install clients — connect machines to your headscale server
Triggers
Load this when you hear "Tailscale," "Headscale," "tailnet," "mesh VPN," "WireGuard mesh," or "self-hosted VPN infrastructure."
Requirements
Bash, Python 3.8+, jq, curl. Access to a Headscale server or the headscale CLI. Tailscale client on target machines.
Why Install This Skill
This skill packages practical, reusable guidance for this domain so you can move from a real task to a dependable result without rebuilding the workflow each time.