The default Gmail hook path configured by `clawdbot hooks gmail setup` is `/gmail-pubsub`. Tailscale strips the mount path before proxying, so the request lands on `/` and the hook 404s under the default configuration.
When Tailscale is enabled, always listen on `/` internally and keep the public URL on the configured path (defaulting to `/gmail-pubsub`). This makes default and custom paths work reliably.
Alternative (not implemented here): call tailscale with a full target URL so the backend keeps the path, e.g. `tailscale funnel --set-path /gmail-pubsub http://127.0.0.1:8788/gmail-pubsub`. We did not take this path because it requires changing the CLI invocation to pass URLs (not ports) plus extra validation, which is a larger behavior change.
Peter Steinberger