@ThreeEyedFish said in Can't connect Ipad Pro to OpenVPN. How do I troubleshoot?:
Hi, your iPad (actually, the VPN App) is telling you that XXX.XXX.XXX:1396 doesn't reply.
Your OpenVPN server on pfSense tells you : no one is connecting right now.
Do you have a firewall rule on your WAN that permits incoming connections "from everywhere" to port 1139, using protocol UDP ?
Do you have a router in front of your pfSense ? In that case, the same firewall rule (NAT rule this time) should be placed on this router.
Btw : the OpenVPN server log lines you showed are traces of the GUI questioning the OpenVPN server for connections every 60 seconds.