Tailscale on Windows never restarts after update

Many, many versions ago I could roll out Tailscale upgrades via Microsoft Intune, and it would update all notebooks, and my colleagues never even noticed.

Then, suddenly, it stopped working - Tailscale upgraded, but it did not start up. Because tailscale always just works, none of my colleagues realized that the reason for their connection problems was that tailscale was down. The resolution was always simple: Click the Tailscale icon in the start menu. No errors. (This might have been around 1.14 or 1.16, I don’t remember exactly.)

I think there was even a github issue related to this, but I fail to find it now. I remember a note that this might be fixed with the new MSI installer - which became available recently. So I tested it. It didn’t work. Tailscale successfully replaced the installation, but it didn’t start up again. :frowning:

This happens on all our machines. This happens on about 1/3 of our machines. (The MSI did improve something?) So - this is the reason, why at least where I work, Windows client updates are very slow. Should a future auto-updater have the same problem… well. Better not think about it.

I cannot be the only one. Or can I? What could I be doing wrong? Is this a known Intune issue? (I would totally believe that) Have I missed an important intune setting? Is there a simple workaround, that I just have not found?

Peripherally related:

1 Like

One problem fixed recently may help: the Go facilities to kill the older tailscaled were being used, which didn’t work quite so well on Windows: RDP upgrade issue · Issue #4091 · tailscale/tailscale · GitHub

A change just went in to instead use Win32 APIs to kill the older version. That will be in the 1.22.1 release, expected in the next few days.

1 Like

We had this RDP issue as well, but since moving away from an old TerminalServer I didn’t care too much about it anymore. The observable behavior was different between RDP-issue and no-restart-after-update, but…

I’ll just test it with the next version and see what happens. It it helps, I’ll note it here.

Sadly, that didn’t help. Update of MSI via Intune was automatically deployed, tailscale did update, but not restart.

Our team found the root cause for that. You can follow the issue here:

2 Likes

@Jay I’m sorry to report: Just tested it, and Intune deployment of MSI installer for 1.22.2 (from MSI-installed 1.22.1) exhibited the same behavior: update OK, but tailscale did not restart. (Result of deployment on first of 7 PCs - let’s see how the rest goes).