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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?

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

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Are you aware of any simple examples of this?
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Check out jdiscript; it's a thin scripting frontend for the JDI that can be used with Java, JRuby, or any other jvm language.

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