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hermes-config/skills/devops/tailscale-remote-access/references/agent-auth-workaround.md
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2026-07-12 10:17:17 -04:00

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# Agent-side auth workaround for tailscale up
`tailscale up` blocks until browser auth completes. The agent can't visit the URL.
## Symptom
```
sudo tailscale up
# prints: To authenticate, visit: https://login.tailscale.com/a/...
# hangs forever → timeout after 60-300s
```
Each run generates a fresh URL. The URL from a previous run is stale.
## Workflow that works
1. `tailscale status` — confirms "Logged out" and prints the current auth URL
2. Give the URL to the user
3. `sudo tailscale up 2>&1` in background with `notify_on_complete=true, timeout=300`
4. User authenticates in browser → process exits → agent notified
## Why foreground fails
Foreground `tailscale up` with timeout will always hit the timeout unless the user is fast. Background + notify_on_complete is the right pattern because the agent gets a push notification when auth completes, rather than polling or timing out.
## Auth key alternative
If the user has a pre-generated auth key from the Tailscale admin console:
```bash
sudo tailscale up --authkey tskey-client-<key>
```
This completes instantly with no browser step. Generate keys at https://login.tailscale.com/admin/settings/keys