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I think you might find WinDBG's javascript debugger scripting useful. You can have a script trigger upon a breakpoint, do whatever you need to do (log data, modify values, etc), and the script can then decide whether or not to continue running the app based on whatever logic you provide it. You can find the documentation for it here:
https://docs.microsoft.com/en-us/windows-hardware/drivers/debugger/javascript-debugger-scripting
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