A few days ago Tailscale stopped working on my Mac.

The tray icon was there, but the context menu wouldn’t show up, and I couldn’t login from the command line either.

The regular saviour duo, reinstalling, and rebooting,didn’t do much either.

Looking at the console logs, I could see a weird message:

Received error: fetch control key: Get "https://controlplane.tailscale.com/key?v=73": read tcp [::1]:53635->[::1]:10011: read: connection reset by peer

Hmmm… Who’s the peer? I wondered, What’s listening on port 10011 ?

Running sudo lsof -i -P | grep -i "listen" | grep 10011 shows this:

What’s webfilter?! Turns out it’s an Apple Service for, well, filtering web traffic.

A while back I turned on Screen Time on my phone and added restriction on some of my time sinking habits (social media, news websites etc).

This setting got synced to my Mac, and turned on the web filtering.

Turning it off solves the problem.

Here’s how:

Go to Settings > Screen Time, click on Content & Privacy and make sure Content & Privacy is off:

Reboot and you should be able to login again.