Terry J. Reedy added the comment:
Either tkinter and tkinter.messagebox or subprocess must be imported to display
a message when IDLE is started from an icon, and there is no console. With
subprocess, '''python -i -c "print('Cannot start IDLE (or whatever)')"'''
should work. If nothing else, this would be a way to display a message when
import tkinter fails.
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<http://bugs.python.org/issue25514>
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