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When there's a problem with opening some file with the default program associated with its type (when clicking a file or typing filename and pressing ENTER at the command line) I'd like Windows to try to open this file with another program. How do I do this?

This is a follow up to my question How to prevent “Open With” dialog window when opening file from command window?

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You can have more than one application assigned to any given extension, but there is not a built-in way for Windows to have more than one default application for any given extension.

Other applications would be listed under the "Open With..." option in the right-click menu.

When you think about it, it would be very difficult to implement such a system for several reasons. One is that there are many ways programs may fail to load, not all of those ways are obvious or visible to the OS. What the OS may think is "normal" for an application is not always what the application (or you) may think is normal, and vice versa.

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