Tailscale auth lost after every sysupgrade

Tailscale question here…

I notice after every sysupgrade, the Tailscale auth is lost.

I have been using the “auth key” method, generating the key on Tailscale dashboard and then disabling key expiration for my rutx11. This works fine, but once I upgrade (e.g. today to 7.07.2), the dashboard shows “key expired” and the RUT page shows “invalid auth”.

I can’t just re-auth at this point, it doesn’t work- and after reboot the device is back to “needs auth” again. The only way to “fix” is to delete the device from Tailscale’s dashboard, and then go through the setup all over again from the beginning.

I also tried updating tailscale on the RUTX11 to 1.68.0 using tailscale update from ssh. Any idea what’s wrong here? It seems like maybe some private key or config file is not being preserved?

I notice /lib/upgrade/keep.d/tailscale contains:


so that seems right, but maybe there’s something else that needs to be added there?

Before this topic expires, anyone got any ideas here? Fwiw, this issue does not seem to occur when using the “Use login url” method.

Fwiw, switching to the “Use login url” method has survived 2 sysupgrades now. My test unit is on 7.07.3 now.

But, probably worth noting the issue when using auth keys—there may be a bug there causing it to lose the credentials after upgrades.

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