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The context menu for a .py file in file explorer is only giving the Choose default program... option in the context menu. Currently it runs it with python.exe by default. If I change the default program from the menu, open with still lists only choose... The choose program menu behaves normally. I only have this problem with .py associations as far as I know. Since I do have a default program this does not seem to be the same problem as this or similar

How do I get the options to open with notepad, sublime, etc. to show up on the open with list?

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I think what you're trying to do is to add items to the Open With menu.

From another superuser question:

Make sure your application has disk:\path_to\your_app.exe.ApplicationCompany string with any meaning e.g. Soopa-troopa soft in [HKEY_CLASSES_ROOT\Local Settings\Software\Microsoft\Windows\Shell\MuiCache].

After creating this registry key open desired file with your application and it will appear in Open with list.

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