On some public networks, my Wireguard VPN just doesn't work. Although I can connect to my server using SSH, so I assume the network was configured to block certain ports or how else can it block VPN connections?
Many networks block UDP ports, which is what wireguard uses. If you can configure the serverside part of the VPN, you could try running it on port 123, which is used for the network time protocol (ntp), which also uses UDP and is open nearly everywhere
Are you familiar with Tailscale? I think it reverts to tunneling over WireGuard over HTTPS in cases like this — I might be wrong, but I might block UDP on myself to test this out.
No, you're right! They have the best name, DERP relays lol. When tailscale can't find a node over UDP , it switches over to TCP and runs the encrypted traffic through the DERP relays.