Hi @pnelson, this is Argun, Quinn's Bluetooth colleague (while I don't have a transceiver in my head, it is not for lack of trying)
I have been discussing your issue with the Bluetooth team, and while we are not dismissing the possibility of a bug, it is possible that the pairing process in different app contexts are behaving differently.
Except we are not able to understand what exactly the conditions are when your app works, and when it doesn't, and when it gets the one error, and when it gets the other. There are also other conditions that might effect the issue, like whether both the Mac and the phone are logged in to the same iCloud account or not (changes pairing details)
To that end, we would like some more info with a sample app, and exact repro steps, and some logs.
So, first please go to https://developer.apple.com/bug-reporting/profiles-and-logs/ and follow the instructions for Bluetooth for macOS and iOS to install a logging profile on each of your devices.
Then, once the logging profile is installed:
reproduce the problem, keeping track of the actual time of the actions you take and the result you see.
If you are going to try the GUI, Menu only, Headless options, please keep a detailed log of what test you have conducted at what time, so we can keep track.
Once the problem is reproduced, follow the instructions at the above link to trigger a sysdiagnose
You don't need a separate sysdiagnose for each test, if you are able to run through the whole set within 30 minutes and immediately trigger a sysdiagnose. If it is going to take longer, please trigger separate sysdiagnoses on both ends after each test, and make sure you mark which log file is which.
Also please indicate the iCloud login state of the two devices. And if you can, test with both logged in to the same account and without.
If you can also attach a sample project that we can build in all the configurations that you are testing, we can see and understand what exactly it is you are doing.
Once you have all this ready, please file a Feedback Report at https://feedbackassistant.apple.com/
Once done, please post the Feedback ID here, and make sure to @mention me so I can route the issue right away.
Argun Tekant /
WWDR Engineering /
Core Technologies