Tailscale stopped working on Windows 7 after Sep 30th


I have an old Windows 7 machine that I use to connect to my home PC when I am away. Tailscale on it stopped working after Sep 30th. Nothing happens after clicking on Log In.

I suspected it’s a certificate issue because opening the Tailscale website in Chrome resulted in a HTTPS warning. After some investigation it turned out this was because the expiration of the DST Root CA X3 certificate.

I downloaded the two new root certificates from Lets Encrypt as well as the intermediate one. After this, I no longer received HTTPS warning in Chrome, but Tailscale still doesn’t work.

Executing “tailscale cert tailscale.com” (just to see if basic communication works) ends up in HTTPS handshake timeout.

Do you have any suggestions on what else I can do?

Sounds like you’re running into some LetsEncrypt cert issues. On newer versions of Windows, this should recover on its own since Windows properly updates its certificate store. On older Windows like your Windows 7, more invasive techniques are needed.

We plan to issue a new v1.14.x build with a workaround. In the meantime, can you try our unstable build, which has a test version of the patch that should fix it for you? https://pkgs.tailscale.com/unstable/#windows

Thanks for the response! Sadly, the unstable build did not fix the issue. Is there anything I can do to assist you in reproducing the issue?

Just to let all know that version 1.16 fixed this issue.