automations/deployments/headscale

headscale

Headscale — a self-hosted Tailscale control server — behind Caddy, with OIDC login delegated to pocket-id.

Prerequisite

Register an OIDC client in pocket-id's admin UI with redirect URI:

https://${HEADSCALE_DOMAIN}/oidc/callback

Then paste its OIDC_CLIENT_ID / OIDC_CLIENT_SECRET below.

Required .env values

Variable	Notes
HEADSCALE_DOMAIN	Public hostname (e.g. hs.example.com). Clients connect here over HTTPS.
ACME_EMAIL	Let's Encrypt registration email.
TAILNET_DOMAIN	MagicDNS suffix (e.g. tail.example.com). Must differ from HEADSCALE_DOMAIN.
POCKETID_DOMAIN	OIDC issuer hostname (your pocket-id).
OIDC_CLIENT_ID / OIDC_CLIENT_SECRET	From the pocket-id client above.

The deploy substitutes these into config.yaml from the embedded template. See .env.example.

Deploy

./automations.sh        # Deploy on this host → deploy: headscale

Or build + run the self-contained artifact:

./build.sh
scp deploy.sh root@host:
ssh root@host 'bash deploy.sh'
# non-interactive: pass HEADSCALE_DOMAIN, ACME_EMAIL, TAILNET_DOMAIN,
#   POCKETID_DOMAIN, OIDC_CLIENT_ID, OIDC_CLIENT_SECRET, SKIP_PROMPTS=1

Unattended provisioning: cloud-init.yml.

DNS for HEADSCALE_DOMAIN must resolve to the host and 80/443 be reachable before deploy.

Headplane (web UI)

Headplane ships in the stack, served by Caddy at https://HEADSCALE_DOMAIN/admin. It runs API-only — it talks to the headscale API with a key and does not get the Docker socket, so it can't control the host. deploy.sh mints the headscale API key automatically on first deploy (stored in .env) and generates headplane.yaml.

Login: to use OIDC via pocket-id, register a second OIDC client in pocket-id with redirect URI:

https://HEADSCALE_DOMAIN/admin/oidc/callback

and pass HEADPLANE_OIDC_CLIENT_ID / HEADPLANE_OIDC_CLIENT_SECRET (prompted by the launcher, or set in .env). Leave them blank to use headplane's API-key login instead. Pin the image with HEADPLANE_TAG (defaults to latest).

headplane integration is version-sensitive; if the UI doesn't come up, check docker compose logs headplane and verify headplane.yaml / the minted HEADPLANE_HS_API_KEY in .env.

ACL policy

A starter ACL ships in policy.hujson (installed to $STACK_DIR/policy.hujson on first deploy; your edits survive re-deploys). headscale uses Tailscale's legacy acls format, not the newer grants syntax from the Tailscale admin console — the bundled policy is that default translated over (per-user self-access, a tag:shared everyone can reach, and SSH to your own devices). Some pieces (autogroup:self, the ssh block) are newer/experimental in headscale; a permissive fallback is included in the file.

$EDITOR /srv/headscale/policy.hujson
headscale policy check                          # validate (host CLI wrapper)
cd /srv/headscale && docker compose restart headscale   # apply