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