It has nothing to do with clang being command line. It consists of many binaries, all of them untrusted. Any time new dynamic lib is loaded Mac stops the process and complains. Then you need to do manual stuff, as you can’t automatically trust a binary, for obvious reasons. This happened almost two years ago, maybe clang got apple certificates or some shit to combat the issue. But my point was that every OS update on Mac brings annoying issues for developers.

Depends on what you are doing. My company was using clang for c++ compilation and it was a drag to make all this clicks for each .so every is update. And there is no way to automate the process. And those occasional compatibility breaks didn’t help either.