After booting Windows 10, Tailscale connections fail until I reconnect Tailscale

Whenever I boot Windows for the first time, my machine can’t connect to any other Tailscale IPs. And other machines can’t connect to me. It’s as if Tailscale is down. But tailscale ping some-other-machine works correctly.

But I found a workaround: right-click on the Tailscale icon in the bottom-right taskbar, click “Disconnect”, then “Connect”. Incoming and outgoing Tailscale connections work perfectly after that.

I originally thought this was a Windows Firewall issue, but the disconnect/connect workaround confuses me. How do I continue troubleshooting? Is this a known issue? I’d like to stop using this workaround because it won’t work on unattended boots, and it’s annoying to remember after a reboot.

I’m running Tailscale 1.26.0 on Windows 10 Pro (10.0.19043 Build 19043). I also have some network adapters related to TAP, VPNs, and VirtualBox installed.

This problem doesn’t happen on another Windows 10 machine (a laptop) that I also use.