From: Matthias Georgi Date: 2006-02-24T09:53:34+09:00 Subject: Re: Q: How to initialize debugger's state when starting A short hack. Make a copy of debug.rb and put these lines right after the Context class. class Context alias original_readline readline def readline(prompt, hist) @rc_file ||= File.readlines("debug.rc") if @rc_file.empty? original_readline(prompt, hist) else @rc_file.shift end end end Now create a file debug.rc with your desired breakpoint: b 100 b 200 Start the debugger: ruby -r./debug myscript.rb