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Created attachment 103989 [details] simple project explaining the problem I made 2 simple sources one (newmain.rb) requiring the other (File2.rb). Setting a breakpoint in newmain.rb will break at the line. Stepping into the require will eventually get you into File2.rb. I then did put a breakpoint in File2.rb and started the debug session again. The first breakpoint did stop, the second did not..
The project was in the next directory. d:\nb\delf\NetBeans\RubyProject2 I was doing a similar thing in another directory c:\projects\delft\NetBeans And debugging was possible !?