Today my macOS machine installed a (presumably) recent App Store upgrade for Tailscale. I wasn’t aware until I realised Tailscale wasn’t connected with everything in the macOS menu greyed out except the “Log in…” option.
Clicking on the Login option did nothing despite numerous attempts, closing and re-opening the app and even removing it and reinstalling.
It wasn’t until I rebooted the machine that Tailscale started working again without any interaction required.
Is this a known problem?
We actually hadn’t heard about this. If you can tell us your tailscale IP address and the approximate time of the problem, we can check our telemetry to see if it matches any known bugs or is a new one. If you like, email the information privately to support at tailscale.com. Thanks!
I’ve just seen this happen again with the v1.4.5 that updated from the Appstore. The app is logged out and clicking on “Log in” in the menu does nothing. I’ll email support as requested.
I did email support and it prompted me to debug a bit more and I uncovered a couple of DNS issues on the machine itself. Console.app on the Mac is extremely handy in this situation itself and showed that Tailscale simply couldn’t resolve login.tailscale.com.
It would probably be helpful if the App alerted when login fails for this reason, and it also seems necessary to restart the App after DNS changes, but this may just be a macOS DNS caching thing.
Hello,
We have created a Feature request for showing the clear error if the app. fails due to this issue https://github.com/tailscale/tailscale/issues/1415.
Please subscribe to it for receiving future updates.
Thank you,