vault-sync: 2026-09-13 12:07 (jimmy)
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title: Tailscale / Headscale Cheat Sheet
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date: 2026-09-05
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type: reference
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tags: [tailscale, headscale, vps, network, ops]
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source: ~/src/Tailscale-configs/README.md
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---
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# Tailscale / Headscale — Cheat Sheet
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Homegrown copy of the repo README (`~/src/Tailscale-configs/README.md`) for vault reference. Join/rotate **keys live in the repo's `tailscale_preauth_keys.md` — never in the vault.**
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Private Headscale tailnet (`ai-lab.tailnet`). Control plane is **HTTP** on `http://74.208.111.99:8443`. Do not use `https://` on that port.
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- **Users:** HS_ty (1), HS_tony (2), HS_shared (3)
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- **Nodes:** ubuntu `100.64.0.1` (VPS, HS_shared) · deepblueubu `100.64.0.2` (HS_ty) · desktop-81cbtv2 `100.64.0.4` (HS_tony) · tyubumini `100.64.0.5` (HS_ty)
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- **DNS base domain:** `ai-lab.tailnet` (MagicDNS enabled)
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## CLI Management (run on the VPS)
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```bash
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docker exec headscale headscale nodes list
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docker exec headscale headscale users list
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docker exec headscale headscale preauthkeys list
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docker exec headscale headscale preauthkeys create --user=HS_tony --reusable --expiration=87600h
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docker exec headscale headscale exit-node reset --node=NodeName
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docker exec headscale headscale rename NodeName --new-name=NewName
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docker logs headscale --tail 50
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```
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## Linux Client (run on the node, **not** the VPS; needs sudo)
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Remote nodes use HTTP `http://74.208.111.99:8443`. The VPS itself uses `http://127.0.0.1:8443`. Do **not** use `--force-reauth`.
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```bash
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tailscale status
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tailscale ip -4
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tailscale ping --c 3 100.64.0.1 # flag is --c, not --ping-count
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sudo systemctl restart tailscaled && sleep 4 && tailscale status # clears 1.98.x sticky-TLS hang
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sudo tailscale up --login-server=http://74.208.111.99:8443 # reconnect if offline but logged in
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sudo tailscale logout # then rejoin with the HS_* line from keys file
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sudo tailscale up --login-server=http://74.208.111.99:8443 --auth-key=<key>
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```
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## Windows Client (DESKTOP-81CBTV2, PowerShell **as Administrator**)
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`.\\tailscale` only works after `cd` to the install folder. No `--force-reauth` (hangs; doesn't rotate keys).
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```powershell
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cd "C:\Program Files\Tailscale" # fallback: "C:\Program Files (x86)\Tailscale"
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.\tailscale status
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.\tailscale ip -4
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.\tailscale ping --c 3 100.64.0.1
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Restart-Service Tailscale; Start-Sleep -Seconds 4; .\tailscale status # clears sticky-TLS hang
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.\tailscale up --login-server=http://74.208.111.99:8443 # reconnect if offline but logged in
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.\tailscale logout # then rejoin with the HS_tony join line
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.\tailscale up --login-server=http://74.208.111.99:8443 --auth-key=<key>
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```
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### Windows common errors
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- `.\tailscale` not recognized → `cd` into `C:\Program Files\Tailscale` first (or x86 path).
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- Must be PowerShell **as Administrator** (normal window can't restart the service / change state).
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- `--force-reauth` hangs (no browser / OIDC). Leave it off: restart the service, or `up` with the HTTP login-server.
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- `https://74.208.111.99:8443` fails (SSL / wrong version). Control plane is **HTTP**.
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- `--login-server=http://127.0.0.1:8443` on Windows does nothing useful — VPS-only address. Remotes must use `http://74.208.111.99:8443`.
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- Status LoggedOut → reconnect without a key won't finish. Logout then use the HS_tony join line.
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- Headscale shows node offline / last seen days ago → **ping the 100.64.x address first**; last-seen freezes when the map stream drops (not proof the peer is down).
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---
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## Related
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- [[Call-2026-08-15-Tony]] — Tailscale/Headscale repair session on the call
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- Repo (source of truth + keys): `~/src/Tailscale-configs/`
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