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fix(headscale): make the server deployable and manage its config in git - #483

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@anatolinicolae anatolinicolae commented Oct 4, 2026 •

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Summary

Headscale on tower could not have started. The documented config.yaml used keys that v0.29 removed, and headscale configtest rejects it. The deploy still reported success, because docker compose up -d returns before the container exits.

This PR puts the server config and access policy in git, checked in CI by the pinned image. It also snapshots the database before every deploy and adds optional MagicDNS. The repository is public, so tower's hostname, its MagicDNS domain and the ACME email come from secrets and are not committed.

Before merging: add the TOWER_HOSTNAME secret to the tower environment, as a bare lower-case FQDN. Without it the OpenTofu apply stops at variable validation (an unset secret arrives as an empty string), and the Headscale stack is skipped. The optional TOWER_ACME_EMAIL and TAILNET_BASE_DOMAIN secrets are described in tower/docs/setup.md. Then run the pre-promotion checks in tower/docs/headscale-setup.md on tower.

Changes

  • Hostname from a secret. TOWER_HOSTNAME is the DNS record name in OpenTofu (var.tower_hostname, sensitive and validated). The system/headscale role writes it into the stack's .env as HEADSCALE_SERVER_URL / HEADSCALE_TLS_LETSENCRYPT_HOSTNAME, and Headscale reads those in place of the config keys. In the Cloudflare provider name updates in place, and relative-vs-FQDN drift is suppressed, so the record is not recreated.
  • Config as code. tower/containers/headscale/config/config.yaml and policy.hujson are mounted read-only. The policy is {}, Headscale's allow-all default, so access is unchanged. A fingerprint of config/ goes into .env, so a config or policy change always recreates the container, even when a deploy is retried. Update checks are disabled, so the healthcheck doesn't poll GitHub.
  • MagicDNS (optional). TAILNET_BASE_DOMAIN turns it on; nodes become <node>.<base domain>. The base domain is the only search domain, with no split or global nameservers, so Linux with systemd-resolved, macOS and iOS all stay in split mode: only names under the base domain go to Tailscale. override_local_dns stays false. The role rejects a malformed value, and a base domain that is tower's hostname or a parent of it (Headscale would refuse to start).
  • ACME email (optional) from TOWER_ACME_EMAIL. DERP region moved to 969 / eu-1, inside the 900–999 range Tailscale reserves for self-hosted relays.
  • Pre-deploy snapshots. Before every deploy, system/headscale takes an online SQLite backup (checked with PRAGMA quick_check) plus the private keys, keeping 14. Each is built under a .partial name and renamed only when complete. Headscale 0.29 won't open a database migrated by a newer minor, so this is the rollback point for an upgrade.
  • Legacy config. The hand-written config.yaml is renamed to config.yaml.pre-git in post_tasks. That happens only once the running container no longer mounts it.
  • Container hardening. read_only: true, a tmpfs for the unix socket, and a headscale health healthcheck.
  • CI. ci/headscale-check.sh is the Headscale config job, also run by ci/validate.sh. It runs configtest, both plain and with MagicDNS and the email set via env, plus policy check, from the pinned image with no network and placeholder values. It also fails if a hostname is committed into the config. On pull requests the job runs the check only when the Headscale stack, the script or the workflow changed; otherwise it skips and still reports success, so it can be a required check without blocking unrelated PRs.
  • Renovate. One PR per Headscale minor, since skipping a minor is refused. The upgrade checklist rides in each PR body.
  • Docs. Rewritten runbook covering pre-promotion checks, first start, MagicDNS behaviour per platform and per-node opt-out, upgrades, rollback order, backup/restore, and why Headscale's users and nodes are not managed by OpenTofu. Identifying details are replaced with placeholders, and the public-repo convention is recorded in CLAUDE.md.

Validation

  • yamllint, ansible-lint (production profile), zizmor, tofu fmt and tofu validate pass.
  • The Headscale check passes. Negative controls fail as expected: the old documented config, a broken policy, a key removed in 0.29, a missing hostname, a hostname committed to the file, and a base domain that is a parent of the hostname.
  • The tower_hostname validation and the role's checks reject malformed values and never print them.
  • Locally against a live container: snapshot, prune and partial cleanup; .env writing; a config fingerprint that recreates the container only when config changes; legacy-config retirement against main's old compose; the no-secret skip; and the documented restore.
  • End to end with MagicDNS: a real Tailscale 1.102.5 client registered against Headscale started from the role-written .env received the MagicDNS suffix and resolved its own MagicDNS name.
  • The CI change detection was run against simulated GitHub merge commits: Headscale, image-bump and policy-only changes run the check; docs-only and other-stack changes skip it.
  • No commit in this PR adds an identifying string.

🤖 Generated with Claude Code

https://claude.ai/code/session_016HysJLPZgnKF7T8FnLhJg6

Summary by CodeRabbit

  • New Features
    • Added an automated Headscale coordination and relay service for connecting devices over IPv4 and IPv6.
    • Added configurable service hostname and optional MagicDNS settings, along with automated database and key snapshots and health monitoring.
  • Bug Fixes
    • Added configuration and access-policy checks to validation; unrelated pull requests skip the Headscale-specific check.
  • Documentation
    • Updated setup and node-registration guides with enrollment, connectivity troubleshooting, upgrades, backups, and recovery instructions. Documented service address, client requirements, and operational checks.

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📝 Walkthrough

Walkthrough

Tower now has a configurable Headscale service managed by Ansible and Docker. The changes add committed Headscale configuration and policy, hostname and DNS inputs, database snapshots, isolated configuration checks, and updated deployment and node-operation documentation.

Changes

Headscale deployment and operations

Layer / File(s) Summary
Hostname and DNS inputs
tower/terraform/variables.tf, tower/terraform/dns.tf, tower/terraform/terraform.tfvars.example, .github/workflows/tower-tofu-apply.yml, .github/workflows/tower-ansible-deploy.yml, tower/docs/setup.md, tower/ansible/roles/system/headscale/defaults/main.yml
Adds a validated tower_hostname input and uses it for the DNS record. Passes the hostname and optional ACME and DNS settings to deployment.
Headscale configuration and container
tower/containers/headscale/config/*, tower/containers/headscale/docker-compose.yml, tower/ansible/roles/system/containers/defaults/main.yml
Adds Headscale configuration and policy files. Compose mounts the config directory read-only, uses an environment file, sets a read-only root filesystem, and adds a health check.
Ansible deployment and database snapshots
tower/ansible/playbook.yml, tower/ansible/roles/system/headscale/*
Adds the Headscale role and its post-task for retiring legacy configuration. The role validates settings, writes the stack environment file, creates SQLite and key snapshots, and prunes snapshots beyond the configured retention count.
Pinned-image configuration checks
ci/headscale-check.sh, ci/validate.sh, .github/workflows/validate.yml, renovate.json, README.md, CLAUDE.md
Adds offline config and policy checks using the image pinned in Compose. Adds the check to local and CI validation, fails local validation when Docker is unavailable, and adds Headscale image upgrade instructions.
Tower and Headscale operating guides
README.md, CLAUDE.md, tower/docs/headscale-nodes.md, tower/docs/headscale-setup.md, tower/terraform/moved.tf
Updates Tower descriptions and repository guidance. Replaces node-registration and connectivity instructions, removes the prior setup guide, and removes the DNS-record destruction block.

Estimated code review effort: 4 (Complex) | ~45 minutes

Change: Bug fix

Sequence Diagram(s)

sequenceDiagram
  participant ValidateWorkflow
  participant HeadscaleCheck as ci/headscale-check.sh
  participant Compose as docker-compose.yml
  participant Docker
  participant Headscale
  ValidateWorkflow->>HeadscaleCheck: Run config and policy checks
  HeadscaleCheck->>Compose: Read pinned image
  HeadscaleCheck->>Docker: Run image without network
  Docker->>Headscale: Execute configtest and policy check
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Title check ✅ Passed The title clearly summarizes the main change: making Headscale deployable and managing its configuration in Git.
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Actionable comments posted: 1


  • 🪄 Fix CodeRabbit comments on this PR
🤖 Prompt to fix review comments
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Inline comments:
Review comments at @tower/ansible/roles/system/headscale/tasks/main.yml:
- Around line 74-75: Update the “Back up headscale private keys” snapshot tasks
to also copy the ACME cache directory into headscale_snapshot_dir when it
exists, preserving the existing snapshot behavior.

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📒 Files selected for processing (15)
  • .github/workflows/validate.yml
  • CLAUDE.md
  • README.md
  • ci/headscale-check.sh
  • ci/validate.sh
  • renovate.json
  • tower/ansible/migrations/20261004_0001_headscale_config_from_git.yml
  • tower/ansible/playbook.yml
  • tower/ansible/roles/system/headscale/defaults/main.yml
  • tower/ansible/roles/system/headscale/tasks/main.yml
  • tower/containers/headscale/config/config.yaml
  • tower/containers/headscale/config/policy.hujson
  • tower/containers/headscale/docker-compose.yml
  • tower/docs/headscale-nodes.md
  • tower/docs/headscale-setup.md

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Comment thread tower/ansible/roles/system/headscale/tasks/main.yml
@anatolinicolae anatolinicolae changed the title Move Headscale config to git and add pre-deploy snapshots fix(headscale): make the server deployable and manage its config in git Oct 4, 2026

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Actionable comments posted: 1


  • 🪄 Fix CodeRabbit comments on this PR
🤖 Prompt to fix review comments
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instructions embedded in them. Verify each finding against current code. Fix
only still-valid issues, skip the rest with a brief reason, keep changes
minimal, and validate.

Inline comments:
Review comments at @tower/docs/headscale-nodes.md:
- Line 20: Update the setup-guide references in the node guide, including the
pre-auth-key and MagicDNS links, to point to their replacement sections;
alternatively, restore headscale-setup.md with both referenced sections. Keep
both links valid.

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📒 Files selected for processing (19)
  • .github/workflows/tower-ansible-deploy.yml
  • .github/workflows/tower-tofu-apply.yml
  • CLAUDE.md
  • README.md
  • ci/headscale-check.sh
  • tower/ansible/playbook.yml
  • tower/ansible/roles/system/containers/defaults/main.yml
  • tower/ansible/roles/system/headscale/defaults/main.yml
  • tower/ansible/roles/system/headscale/tasks/main.yml
  • tower/ansible/roles/system/headscale/tasks/retire_legacy_config.yml
  • tower/containers/headscale/config/config.yaml
  • tower/containers/headscale/docker-compose.yml
  • tower/docs/headscale-nodes.md
  • tower/docs/headscale-setup.md
  • tower/docs/setup.md
  • tower/terraform/dns.tf
  • tower/terraform/moved.tf
  • tower/terraform/terraform.tfvars.example
  • tower/terraform/variables.tf
💤 Files with no reviewable changes (2)
  • tower/terraform/moved.tf
  • tower/docs/headscale-setup.md
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Comment thread tower/docs/headscale-nodes.md
claude added 15 commits October 6, 2026 19:05
The repository is public, so tower's FQDN, the tailnet's node names and
what those nodes run should not be in it.

- New TOWER_HOSTNAME environment secret, a bare FQDN. OpenTofu uses it as
  the DNS record name through a required, sensitive var.tower_hostname.
  In the Cloudflare provider only zone_id and type force replacement, and
  a zone-relative name and its FQDN are treated as equal, so the record
  is not recreated.
- Drop the applied `removed` block for the previous DNS record: a
  resource left in state with no config is destroyed anyway, and its
  address named an old host.
- Remove node names and hardware/OS details from the Headscale docs, add
  the secret to setup.md, and record the public-repo convention in
  CLAUDE.md.

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>
Claude-Session: https://claude.ai/code/session_016HysJLPZgnKF7T8FnLhJg6
The config.yaml documented in tower/docs/headscale-setup.md could not start
headscale v0.29.4: it used `dns_config` (removed in 0.23), `ip_prefixes`
(no longer read, leaving no prefix configured) and left MagicDNS on without
a base_domain. `headscale configtest` rejects it. The deploy still reports
success, because `docker compose up -d` returns before the container exits.

- Commit config.yaml and policy.hujson under containers/headscale/config/
  and mount that directory read-only. Neither holds secrets or the
  hostname: system/headscale writes HEADSCALE_SERVER_URL and
  HEADSCALE_TLS_LETSENCRYPT_HOSTNAME into the stack's .env from
  TOWER_HOSTNAME, and headscale reads them in place of the config keys.
  The stack deploys only when .env exists (env_file: true); without the
  variables headscale refuses to start. The policy is `{}`, the same
  allow-all Headscale applies with no policy, so access is unchanged.
- Run the container read_only with a `headscale health` healthcheck.
- system/headscale runs before system/containers. It makes the data and
  backup directories 0700 and, before every deploy, takes an online
  SQLite snapshot (checked with PRAGMA quick_check) plus the private keys.
  A Renovate minor bump that migrates the DB therefore has a rollback
  point; 0.29 refuses to open a DB migrated by a newer minor.
- Rename the hand-written config.yaml to config.yaml.pre-git, but only in
  runs that redeploy the stack, because an untouched old container still
  bind-mounts it.

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>
Claude-Session: https://claude.ai/code/session_016HysJLPZgnKF7T8FnLhJg6
ci/headscale-check.sh runs `headscale configtest` and `policy check` from
the image pinned in the compose file against the committed config, with no
network access, a tmpfs data dir and a placeholder hostname supplied the way
tower's .env supplies the real one. It also fails if a hostname is committed
into config.yaml. This is what fails a Renovate bump whose release removed
a config key, before it can crash-loop on tower. Added to validate.yml and
ci/validate.sh.

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>
Claude-Session: https://claude.ai/code/session_016HysJLPZgnKF7T8FnLhJg6
Headscale 0.29+ refuses to start after a skipped minor version, so set
separateMultipleMinor for headscale/headscale and carry an upgrade
checklist in each PR body.

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>
Claude-Session: https://claude.ai/code/session_016HysJLPZgnKF7T8FnLhJg6
- `preauthkeys create` needs `--user <ID>` and `debug node-key` does not
  exist; both documented commands fail on v0.29.4.
- Add a pre-promotion checklist, first start, upgrade, backup/restore and
  external verification steps.
- Record the OpenTofu evaluation: the official Tailscale provider speaks
  Tailscale's /api/v2 admin API, which Headscale does not implement; the
  community provider supports Headscale 0.28.x only.
- README/CLAUDE.md: tower is the Headscale server, not a WireGuard
  endpoint; headscale needs NET_BIND_SERVICE, not NET_ADMIN; list the new
  check under validation.

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>
Claude-Session: https://claude.ai/code/session_016HysJLPZgnKF7T8FnLhJg6
From CodeRabbit's security architecture review:

- A config- or policy-only change was applied only by the shared restart
  handler. If a run died before handlers fired, the retry copied nothing
  new and never notified, leaving the old policy loaded. The role now
  writes a fingerprint of the committed config/ directory into .env
  (CONFIG_SHA256). A changed environment makes `compose up` recreate the
  container, so every run converges. Tested: an unchanged rerun keeps the
  container; a policy-only change recreates it and loads the new policy.
- Snapshots are built under .<ts>.partial and renamed only after the DB
  check and key copy succeed, so an interrupted attempt can no longer take
  one of the kept slots. Leftover partials are removed on the next run.
- Rollback docs: merge the image revert first (the old image refuses the
  migrated DB, which changes nothing), then restore. Restore with
  `compose up -d`, not `start`, which would reuse the newer-image
  container and migrate the restored DB again.

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>
Claude-Session: https://claude.ai/code/session_016HysJLPZgnKF7T8FnLhJg6
A missing GitHub secret reaches the job as TF_VAR_tower_hostname="", which
OpenTofu treats as a set value. The required variable therefore did not stop
the unattended apply, which would have planned an in-place rename of the DNS
record to "". var.tower_hostname now validates as a bare lower-case FQDN,
and the Ansible assert uses the same pattern. Tested: "", single labels,
upper case, a scheme and a trailing dot are rejected, and the error does
not print the value (the variable is sensitive).

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>
Claude-Session: https://claude.ai/code/session_016HysJLPZgnKF7T8FnLhJg6
The rename of the old single-file config ran in system/headscale, before
system/containers recreated the stack on the new compose. If the run failed
in between, the old container was left bind-mounting a path that no longer
existed, and its next start would fail (dockerd recreates the missing
source as an empty directory).

The rename now runs from the playbook's post_tasks, and only once the
headscale container exists and none of its mounts is the old file.
Tested against main's compose: skipped while the old container still
mounts the file, renamed after the redeploy, a no-op on rerun, and skipped
when there is no container.

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>
Claude-Session: https://claude.ai/code/session_016HysJLPZgnKF7T8FnLhJg6
headscale's CLI initialisation (cmd/headscale/cli/root.go in v0.29.4) asks
the GitHub API for the latest release on every invocation unless
disable_check_updates is set. That includes the `headscale health`
healthcheck, so tower would make ~2,900 unauthenticated API calls a day,
well past GitHub's 60/hour limit. Set disable_check_updates: true; Renovate
already tracks releases.

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>
Claude-Session: https://claude.ai/code/session_016HysJLPZgnKF7T8FnLhJg6
From the adversarial review of this PR:

- Rollback: restore the snapshot the upgrade deploy itself took. It is
  taken before the image switch, so it is the newest pre-migration copy.
  The doc said to skip it.
- netcheck: only `UDP: true` plus a STUN-mapped IPv4 address proves
  3478/udp is reachable. A region latency is measured over HTTPS when STUN
  fails.
- `policy get` in file mode re-reads the mounted file, so it shows what is
  on disk, not necessarily what is loaded.
- Only keys on headscale's deprecation list are fatal. Other renamed or
  dropped keys are silently ignored, so the config-example diff in the
  upgrade checklist is still required. Correct the comments in the config
  and in ci/headscale-check.sh to say so.
- Changing TOWER_HOSTNAME renames the DNS record in place. The current
  tree does not contain the hostname, but git history may, so pick a name
  that was never committed.
- CLAUDE.md: OpenTofu is pinned at 1.13.x, not 1.12.x.

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>
Claude-Session: https://claude.ai/code/session_016HysJLPZgnKF7T8FnLhJg6
Tailscale reserves region IDs 900-999 for self-hosted DERP (tailcfg/
derpmap.go); the rest belong to its own regions. 969 cannot collide with
one of them if their map is ever added to derp.urls as a fallback. Rename
the region to eu-1; the region code stays `tower`, which is what status
and ping output show.

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>
Claude-Session: https://claude.ai/code/session_016HysJLPZgnKF7T8FnLhJg6
All optional, all from tower environment secrets through the role-written
.env, so nothing identifying is committed:

- TAILNET_BASE_DOMAIN turns MagicDNS on (HEADSCALE_DNS_MAGIC_DNS and
  HEADSCALE_DNS_BASE_DOMAIN). It stays off in config.yaml because
  headscale refuses to start with it on and no base domain.
- TAILNET_SEARCH_DOMAINS (space-separated; viper splits env lists on
  whitespace) become search domains. Each one gets 1.1.1.1, 9.9.9.9 and
  their IPv6 addresses as split nameservers, passed as a JSON map. Without
  them, systemd-resolved nodes route the search domain to 100.100.100.100,
  which has nowhere to forward it, so every name under it fails.
- TOWER_ACME_EMAIL becomes HEADSCALE_ACME_EMAIL.
- override_local_dns stays false, so nodes keep their own resolvers. No
  global nameservers: with override off the client only uses them while an
  exit node is in use.

The role validates every value and fails the deploy, without printing
values, on a malformed email or domain, on a base domain that is tower's
hostname or a parent of it, or on search domains without a base domain.
Headscale would otherwise crash-loop on these. CI also runs configtest with
MagicDNS, split DNS and the email set via env. Tested end to end: a real
Tailscale 1.102.5 client registered against headscale started from the
role-written .env receives the MagicDNS suffix, the search domains and the
split routes, and resolves its own MagicDNS name.

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>
Claude-Session: https://claude.ai/code/session_016HysJLPZgnKF7T8FnLhJg6
The previous commit truncated tower/docs/headscale-setup.md to zero bytes
(an edit script reopened the file for writing before reading it back),
which broke the node guide's links to it. Restore it from the commit before,
plus the two edits that commit intended: the MagicDNS section and the
secrets row in the "who manages what" table. All in-repo anchor links
resolve again.

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>
Claude-Session: https://claude.ai/code/session_016HysJLPZgnKF7T8FnLhJg6
On pull requests the Headscale config job now diffs GitHub's test merge
commit against its first parent (the base branch). It runs the pinned image
only when the PR touches tower/containers/headscale/ (config, policy, and the
compose file whose image pin Renovate bumps), ci/headscale-check.sh, or
validate.yml. Otherwise the job skips the step and still reports success, so
it can stay a required status check. A workflow-level `paths:` filter would
leave a required check pending forever instead. Merge queue and manual runs
always check.

Tested by extracting the step from the workflow and running it in depth-2
clones of simulated test merge commits: this branch, an image bump and a
policy-only change run the check; docs-only and other-stack changes skip it.
The pinned actions/checkout checks out github.ref and github.sha by default,
which on pull_request are refs/pull/<n>/merge and the test merge commit.

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>
Claude-Session: https://claude.ai/code/session_016HysJLPZgnKF7T8FnLhJg6
…cDNS

MagicDNS now pushes only the base domain. The TAILNET_SEARCH_DOMAINS secret
and the split nameservers written for each search domain are removed; the
variable is ignored if still set. A public search domain without split
nameservers would break systemd-resolved nodes (every name under it fails
with SERVFAIL), so the two went together, and the search domains were the
only reason iOS and macOS routed all DNS through Tailscale. Without them
those platforms stay in scoped split mode: only names under the base domain
go to Tailscale.

Public hosts are reached by their full names. The base-domain-only shape is
what CI's MagicDNS configtest now exercises.

Co-Authored-By: Claude Fable 5.1 <noreply@anthropic.com>
Claude-Session: https://claude.ai/code/session_016HysJLPZgnKF7T8FnLhJg6
@anatolinicolae
anatolinicolae merged commit af195d5 into main Oct 6, 2026
@anatolinicolae
anatolinicolae deleted the anatoli/headscale branch October 6, 2026 17:14
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