By the nature of the client mode debugging, you will possibly relaunch eclipse in debug mode (listen) manually because you will do the same with the client application (attaching it to the eclipse listening port using jdwp).
But you also can try create a launch configuration programatically using Eclipse SDK, implementing an algorithm to restart the "listen mode" when the vm exists.
Just a thought , Can you try using:
Your application will be suspended till the time the debugger is attached, that way you would atleast be able to debug right from the entry point to your code.
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