I was doing a lot of debugging the other night and I kept running into issue where I'd set a breakpoint (and it would show in the UI as red), but the debugger wouldn't stop at that point. And if I reset (clear/add) the BP, then it would get hit. This happened quite a few times, but unfortunately I don't have any logs or anything to provide here. I was debugging both vscode itself and an extension and I saw the behavior in both.