Same problem; it seems to be a bug in iOS or Xcode.
Running Xcode 15.0 (15A240d) from Mac AppStore, and it looks like it only happens to devices running 17.0.0 and 17.0.1. Devices running 16.7 can still use wire to debug, and the "Connect via network" checkbox is functional.
I filed a bug report here https://feedbackassistant.apple.com/form-response/31792610 I hope those who facing the same issue can file a report as well to encourage Apple to fix it ASAP.
Update Oct 17,2023: while it has not been fixed by Apple, the workaround in the developer forum worked for me: https://developer.apple.com/forums/thread/737875?answerId=768846022#768846022
- Plug in your device without Xcode running
- Launch Xcode
Update Dec 19, 2023: this is still an issue with iOS 17.2.1 and Xcode 15.2; a better workaround is posted in the developer forum: https://developer.apple.com/forums/thread/737875?answerId=773300022#773300022
- Disconnect Wi-Fi
- Launch Xcode and run debug
- Re-enable Wi-Fi
- Run debug again
If you can disable the VPN on your macOS, make sure you do so; the VPN connection seems to create a lot of problems