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?

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?

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