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Oh goodness, the Windows filepath limit has caused so many headaches at work. Even if you enable longer filepaths, not all applications pay attention to that, since at some point, Microsoft promised a specific filepath length and some applications hard-coded it in, so Microsoft is kind of locked in to supporting that being the default max filepath length. Not sure if any Office applications fall into that camp, but given that most filepath length errors I see are from Windows itself silently failing to finish extracting a zip archive, it wouldn't surprise me!
This really sucks when part of the mandatory cloud file path name is "defense information systems agency". That eats up a lot of the available space.