Product
Tailscale one click: cancel and try again no longer breaks
Cancelling and clicking again while a slow container starts now works. The view shows what it waits for, and the tab always says why.
The Tailscale button could fail for a slow container: if you cancelled and clicked again while the work environment was still starting, the second try broke the first and the tab closed without a word. That is fixed.
Text version
Cancelling stops the running attempt, and a new click reuses the work environment that is already starting. The view names the phase it waits for. A tab that gets no sign-in page says why instead of closing, and after three minutes the view offers a retry.
A cold start of a vm-gvisor container takes about 80 to 110 seconds before Tailscale can begin. In a live test on a fresh box the sign-in page arrived about 40 to 110 seconds after the click, and a cancel with a new click about 40 seconds in still ended with the page. The view now says "Work environment is starting (about 2 min)", then "Tailscale is starting" and "Fetching the sign-in page". Opening the section warms the work environment, so the click finds it up.
A paused container is woken by the same click. If nothing arrives, you get a clear message: the container cannot reach Tailscale, or the page came too late, with a button to try again.