Me and a Friend I room with are trying to play on this server, his username is tyler_eto mine is wafflekai. I can log in just fine, but he can't. I'm wondering if the both of us being on the same IP address is making it so he can't join the server
I can't say for Heroes Reborn, but previously I had a brother that used to login with me on Herocraft with the same ip address and different accounts, and we didn't have any issues. So I am not sure why your having issues, unless its changed for reborn. @Kainzo any ideas?
Edit: try testing whether he can login when your off the server.