This fixed one device for me: Turn off Mac WiFi Put your iPhone in Airplane Mode From XCode Devices&Simulators > Devices: Forget all devices Click + to open Choose a connected device to set up dialog Connect your iPhone via USB Click Okay when asked if you trust the computer (and enter password) Select device and press the Next button Wait for it to sync the cached symbols. Verify that the device shows up in the Connected list Turn on Mac WiFi Turn off Airplane Mode After this, I was also able to sync another phone just by pulling it back into the computer via USB, trusting, and waiting for cached symbols. Prior to this, I spent hours trying all sorts of combinations. I guess killing wifi as the silver bullet in my case.