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Whether I try to flip a selection with the default setting (Alt + Shift) or setting it to a new key, flip will not work for me. I've also tried uninstalling and reinstalling the program.

I am on Windows 10, 64 bit.

Any ideas on how to fix this are appreciated!

Have you tried holding Alt + Shift and left click dragging in the direction you want to flip the selected image? The image interaction bindings under Controls work together with the left mouse button.