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Hi, you can assign one file to only one category. So if you want to have one file (file on server) in e.g. two categories, you need to create two instances of this file:
There will be two files in system but both will use one filename (file on server), e.g.:
File A (title) will use filename: file.zip
File B (title) will use the filename file.zip
So two different files will use the same filname (of course both of them can have the same title)