I’ve run into the same issue. However, I don’t believe that the VPN connection is to blame here. It’s rather that Xcode always tries to connect to the device via network and not via USB, even when the device is connected with a cable to the Mac. The “Connect via network” option is checked by default and connect be unchecked: So this clearly is an issue in Xcode, although I’m not sure if that’s intentional or not. If it is, it’ll severely hinder our ability to debug. The app we’re developing connects to hardware via Wi-Fi. So as soon as the iPhone/iPad used to debug connects to our hardware it’ll leave the network that the Mac used for debugging is on, severing the connection to Xcode. That will leave us unable to debug.