I also ran into this problem, although, unfortunately, I do not know the exact solution, maybe I can offer some information that may be useful.
I (like you, judging by your screenshot) used Cocoapods, and Cocoapods copied resources from containers to the application extension kit after it was signed with code. If the memory works, it somehow interferes with the code signing and, therefore, prevents the application from running under the debugger.
I believe that one of the symptoms of this was that the logs appeared on the Mac console (or the device’s console, which they don’t remember that) say something about “exploding on the device using the old skool [sic] method”.
You could confirm that this is so by removing Cocoapods from your project or any containers that require copying resources after compilation. I believe the solution was to add some special build phase to the extension project, to copy the package resources, and disable all Cocoapods by default.
As a temporary solution, I believe that removing your application from the device should allow you to attach the debugger once, at startup, where the application is installed for the first time. You can also try deleting derived data for your project.
Ben pious
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