When my iPhone is on my local WiFi Xcode sees my iPhone over the network. My Mac Pro development machine is running macOS Server with a VPN server. When I VPN into my Mac Pro from my iPhone my Mac can ping the iPhone over its VPN IP address screenshot (172.22.0.225) and Network Utility is showing that port 62078 (the required port for debugging) is open. screenshot However, when I try to connect via IP in Xcode it says my iPhone is no longer available. screenshot Any suggestions?