Somewhat quick one here, if you’ve just installed Tailscale and it’s stuck in “Starting”, from what I’ve found online there are a couple of different things that can cause this (firewall rules, DNS, other VPN solutions in place interfering), but I’m going to focus on one that I haven’t found many other places and that burned me recently: a previous install of Tailscale.

Recently I was working with someone who’s computer got upgraded to Windows 11, but they also refreshed the hardware at the same time – did some sort of clone to a new box, then did an in-place upgrade – I was not aware of the cloning part, only the new hardware part. I had worked with her in the past to get her remote access to the computer via Tailscale & RDP (everything is on the up-and-up, this is not a ShadowIT situation, her and her husband own a small business and while I’m not able to be their primary IT support, I do help them out with special situations), and with the ‘new computer’ her Tailscale wasn’t connecting anymore. This of course happened randomly one morning when she absolutely needed it to get something done that morning. I hopped on a remote session with her and got Tailscale installed for her again like I’d done with many computers many times in the past, and boom she was able to access her computer remotely again.

Problem solved, right? Well, that evening Tailscale disconnected and she couldn’t access it again. I thought ‘Man, I forgot to select the option for Tailscale to reconnect on reboot, and I bet it ran updates or something’. Well we hopped on a remote session and I tried to set that preference, but Tailscale was stuck in ‘Starting…’, so I was not able to get to the Preferences window. What worried me more though, was the fact that Tailscale seemingly wasn’t connecting properly and although it would allow remote access for a while when I restarted the service, it still would never get past ‘Starting…’ in the Taskbar Menu and would eventually disconnect. I did the standard things, reboot, repair, uninstall/reinstall, looked online and found that firewall rules, DNS, or even competing VPN software could be affecting it. I uninstalled AnyDesk (her regular IT support folks had installed it) and a few other things, made sure everything else looked good but I could not get it to work correctly. I even tried the MSI version of the installer vs the EXE because I found one forum that said it might handle conflicts better with the MSI, but still no luck. At some point in here I found out that it was a clone of the other computer so I figured I was dealing with old Tailscale registry entries or something, so uninstalled again, deleted what I could find and reinstalled but still no luck.

Finally I found on a forum that the logs are stored in C:\ProgramData\Tailscale\Logs and I found in the logs a message that said ‘Unable to connect to the Tailscale coordination server to synchronize….’ and as I was digging into that, I found this Issue Ticket posted on Github – https://github.com/tailscale/tailscale/issues/17863 – indicating the exact issue that I was seeing, but it was happening when installing a new CPU. That Issue Ticket then linked here – https://github.com/tailscale/tailscale/issues/13494#issuecomment-3495108356 – showing the proper file cleanup that should be done when uninstalling/reinstalling Tailscale, the procedure being:

• Uninstall Tailscale
• Delete C:\Program Files\Tailscale
• Delete C:\ProgramData\Tailscale
• Delete C:\Users\xyz\AppData\Local\Tailscale
• Re-install Tailscale

And this solved it for me. As soon as I reinstalled, Tailscale connected like I expected and seems to be working perfectly now. As for a bunch of other people on that thread, it seems like deleting C:\ProgramData\Tailscale was the one causing the most problems.

As a side note for anyone dealing with this, every time I reinstalled Tailscale I needed to delete the previous one out of my Tailscale console or I’d get a duplicate. It was easy enough to clean up if I forgot, delete the previous one, update the name of the new one to remove the ‘-1’ indicating a duplicate and move on, but something worth noting that it’s a little easier to delete it prior to reinstalling Tailscale.