I need to keep building my project until the debugger actually works by stopping on breakpoints. It's really annoying. Some builds stop on breakpoints, some don't. This answer no longer seems to be relevant to my particular issue.
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Not an answer, but I certainly feel your pain. Maybe getting people to post to bugreport.apple.com and to further "upvote" this rdar ("radar") bug will help: https://openradar.appspot.com/43072150 – pestophagous Jul 19 '19 at 20:54
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Please do file bugs, but also, if you can, please include a sample project that shows the problem and instructions for how to run the project to cause the failure. There are enough degrees of freedom in constructing Xcode projects that trying to work from failures described at the level of abstraction of this question or the quoted radar to an actual cause for the failure is often not practical. – Jim Ingham Jul 22 '19 at 18:44
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Same issue, months later. Any solution? – Jeff Apr 28 '20 at 08:31