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If you are used to Wing 101 it might be because the icon for debugging is different - it's the green "play" icon and not the bug icon - and there isn't an icon in the toolbar for running in the Python Shell. The latter is Evaluate File in Python Shell in the Source menu (command name evaluate-file-in-shell in case you want to bind a key to it). The Stop icon appears once you have something running in the debugger but is not shown if nothing is being debugged.