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One issue I've encountered is someone else's software setting PYTHONPATH to their install directory of python. We have some old software that installs and uses python 2.3 scripts and unfortunately this prevents the IDLE shortcuts for newer versions of python from working correctly on the system. This could be remedied with -E being added to the shortcut, but windows doesn't allow me to directly edit the IDLE shortcut, and it hides how IDLE is being launched via Python in the first place, making it a challenge to create my own. I'd remove PYTHONPATH from the system environment variables except I don't know why it's set in the first place.
Suggestion: IDLE safe-mode which runs with -E OR include a batch file for IDLE so that I can easily append my own command line arguments and create my own shortcuts.