Steve Dower added the comment:

I'm not familiar with any of the other proposed solutions - could you link to a 
few?

One important factor is that you need to install the Python Launcher to get the 
context menus (this is the default in 3.5 and later). Associating directly to 
the Python installation just causes conflicts when you install another version, 
so we set them up via the launcher instead. In effect, the launcher is the 
integration point between Windows Explorer and Python, and without it you only 
get the shortcuts.

Installing Python 2.7 and leaving the "Register Extensions" option selected 
will overwrite the context menu from Python 3.5 or later. So if you've 
installed 2.7 after 3.5 then I would strongly recommend running a Repair of 3.5.

Otherwise, answers to Terry's questions would also be helpful. It isn't 
entirely clear how you are "choos[ing] the IDLE application", or if the 
installations were successful.

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Python tracker <rep...@bugs.python.org>
<http://bugs.python.org/issue29014>
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