Thanks here is the bug report": https://feedbackassistant.apple.com/feedback/11010138

I’m not entirely sure this is a bug.  you said: "It does sound like the trusted execution system is caching the negative result from step 4." that sure sounds like not intended behavior which most people would interpret to be a bug ;) Did you file a bug report about it? If so, what was the bug number? Could you let me know how to file a bug?

Unfortunately this is not possible in our case. Why can't Apple fix this bug? Or better yet why can't we just staple command line apps?