Xcode issues pairing to Supervised Devices

We have been using a Supervision Identity successfully over the last few years to allow us to Xcode debug on managed devices. Something has changed in the last few months which we are finding it hard to find a consistent solution to. We can't determine whether it's Xcode 15/iOS version related. Behaviour we see documented below

  • All Macs with the Supervision Identity installed can open the device in Apple Configurator without need for trust acknowledge on the device. Configurator can open and stream the device console.
  • All problematic devices are also registered as a development device with Apple.
  • We have hit and miss connectivity in Finder, On failure it indicates that the trust prompt on the device needs to be accepted. No trust prompt is displayed
  • Developer Mode on the device can't be enabled until we attempt to connect to Xcode
  • Devices that pair successfully in Xcode do so almost immediately. If a device pairs in Xcode it is also visible in the native macOS Console application
  • If a device fails to pair in Xcode we get a spinner and the message

"Xcode has already started pairing with 'iPhone-X'. Select Trust on iPhone-X to complete pairing".

  • The macOS console app reports

"The user has not responded to the pairing request on 'iPhone-X' In neither case is a trust prompt displayed on a device.

  • We are not able to Xcode pair any managed device running iOS 17.x. This includes devices that were successfully paired on iOS16.x then upgraded
  • iOS16.x devices that pair with one Mac successfully will not pair with another Mac with the same Supervision Identity installed.
  • The same behaviour is seen on Ventura and Sonoma Macs
  • Clearing Trusted Computers in IOS Developer Mode has no effect
  • None supervised iOS devices pair successfully on iOS 16 and 17

Has anyone else witnessed similar issues and found a work around ?