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How can I drive the debugging session with some scripting language like ruby? Is there any easier options than using Expect or some similar module with a scripting language?

+1  A: 

You may be able to use JRuby to drive your own debugger via the JPDA API.

McDowell
Are you aware of any simple examples of this?
JtR
No, but: Using JPDA in Java: http://illegalargumentexception.blogspot.com/2009/03/java-using-jpda-to-write-debugger.html Calling Java from Ruby: http://wiki.jruby.org/wiki/Calling_Java_from_JRuby
McDowell