truffleruby
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Can't set breakpoint in core library files
Similar to oracle/graal#5125, core library files won't appear in the "Loaded Scripts" section in the VS Code debugger. You can step into Ruby core library from a user function, which will cause the core library to load in the editor view. But, unlike with standard libraries, setting a breakpoint in this editor will not work when restarting the debugger. As a result, it's rather difficult to debug anything related to the core library.
Are you using --core-load-path in this case or not? If yes, it's most likely the same as https://github.com/oracle/graal/issues/5125.
If not, then the Source doesn't actually have a file that VSCode can open, it's a file from inside truffleruby.jar, so then it sounds like a VSCode issue.
With --core-load-path it worked fine when we tried recently, although one needs to first find such file and they are not all in Loaded Scripts.