I let the cert rollover on my TrueNAS system, and now i am unable to renew it.
So I installed the official Tailscale App in the TrueNAS GUI, authed just fine and generated the cert, then manually copied the contents to a new cert and made it the default one required to login to WebGUI. It worked for me until I figured out a way to automate it...someday.
This time I completely forgot to renew, and somewhere between updating Truenas and the cert expiring, I can no longer enter the shell of the Tailscale App to do it all again.
I've tried the shell form within the webgui, but docker doesn't even seem to be running, so that's a dud, but running the same docker ps command from local machine does, but complicates everything massively.
I've debugged using forum posts and asking AI for suggestions, but got nowhere. HALP
Posted Jun 10, 2026, 4:35 PM UTC