All fine and great with Tailscale until you company places an iOS restriction on external VPNs and your work phone is also your primary phone :(

Usually you can ask for a separate phone for work. I can't stand when personal devices are poisoned with Intune and other company crap.

My work WiFi blocked traffic to port 51820, the default WireGuard port. I was wondering why my VPN started failing to handshake one day. I changed my ports to 51821 that night and back in business. I checked our technology policy and there’s no “thou shalt not use a VPN” clause so no clue why someone one day decided to drop WireGuard traffic on the network.