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I have never had an Open With... option with Firefox. Is there a way to get this functionality

Here is a screenshot of my context menu. Note that shift-clicking or shift right clicking makes no difference. Also, it does not matter what kind of file you click. It does not matter if you have a program associated with the extension or not. Under no circumstances will an Open With... option appear on my machine.

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To the best of my knowledge, there is no "Open With" option in the context dialog. However, you can set up the applications to open the filetype - go to Tools > Options > Applications.

This Mozilla KB has an example with handling emails with a different mail application in FF - configuring your chosen helper app for JPG files will be very similar.

example screenshot from Mozilla KB

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