Why can I not connect to my VPN while on one specific friends WiFi?

I have a VPN hosted on my local network. My friend cannot connect to the VPN/internet when he is on his own WiFi. The VPN works fine when he uses cell data. No idea where to start with trouble shooting here other than maybe the IPS router is blocking something. But that doesn’t make sense to me.

Maybe both networks (the one you are trying to connect from and the one you are trying to connect to) use the same range of IP addresses. The VPN range must be different

Maybe your friend’s router/ firewall is blocking vpn connections.
If you have access to router, go through firewall to see if any vpn or port prohibiting rules exist.

im assuming the following:
friend device ->cellular->your vpn server->internet =ok
friend device ->friend wifi->your vpn server->internet =not ok

What vpn have you setup? openvpn? l2tp?

That was it. Thanks!

Both networks can have the same subset. This issue could be easily overcome with virtual IPs assigned from the VPN server.

Furthermore, if the OP’s friend needs constant VPN access to the OP’s network, then setup a site to site VPN with bypass LAN enabled. Only now I see a need for two different LAN subnets.