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The Testing tool isn't designed to allow access to stdin on the testing process, since it's more for unattended and not interactive tests. One idea is to run your tests in the OS Commands tool (for example by using the Execute items in the Debug menu). Or change the test to throw up a dialog instead.

I'm not sure how specifically the debugger would cause an interaction, since it just runs the same code in the same order. However, it does set up a stdin wrapper so I/O can occur in the Debug I/O tool in Wing, and maybe that is causing a problem. There is a pref to turn that off: Debugger > Advanced > Use sys.std Wrapper. But I think you would also need to check the Debugger > I/O > Use External Console preference so you can interact with the process. That opens a separate console rather than redirecting I/O to the Debug I/O tool.

Please let us know if none of this works.