macOS tailscale logs out after less than 5 mins of signing in
Tailscale on macOS logging out within minutes of signing in (introduced around 1.40.0) was fixed in Tailscale 1.52: the client now restarts itself when the system kills it. If you're on 1.40.x-1.51 and see 'Please log in' loops, upgrade to 1.52 or later.
_Source: gh:tailscale/tailscale#8220 (Tailscale)_