Tailscale + Mosh Recovery (Headless Mac mini)

Problem

After a Tailscale update or daemon restart on a headless Mac mini, mosh sessions break. Common symptoms (any combination):

• tailscale status returns: failed to connect to local Tailscale service; is Tailscale running?
• mosh <host> returns: could not get canonical name for <host>: nodename nor servname provided, or not known, then Connection closed by UNKNOWN port 65535, then Did not find remote IP address (is SSH ProxyCommand disabled?).
• Tailscale GUI app CLI returns: Tailscale.CLIError error 1.
• which tailscale reports a path that does not actually exist on disk.
• tailscale up registers the machine as <hostname>-1 (a duplicate of the original node — IP changed).

The two underlying problems are causally linked: Tailscale daemon trouble forces a re-auth → new Tailscale IP → existing mosh-server processes are bound to the old IP and become unreachable.

Context / Triggers