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Sadly, on the only machine that I would have wanted this on, where I didn't have root access, this has never worked for me.

I should try to recreate the logs and issue for the tailscale folks.

Our customers at Render run Tailscale in user mode every day. Here's the repo they use: https://github.com/render-examples/tailscale.

I had issues with it as well, was following the Tailscale guide for getting userspace running in Azure App Service and I could not get it to work.