Hasnain says:

This was a really interesting debugging story.

“This investigation reinforced the breadth of interestingly (for some values of “interesting”) configured clients that Tailscale (or any other service) has to deal with. While this was not the gnarliest bug ever, it was satisfying to keep accumulating breadcrumbs that explained more and more behaviors (e.g. the 5 minute timeout in the autocert library). And by closing it out, we were able to continue on our quest to make things just work.”

Posted on 2022-09-15T20:06:40+0000