As we know this is a checkbox that tells iTunes to, well, do exactly what it says. I almost always have this ON since iTunes does a good job of maintaining a sensible and logical file and folder structure for the media storage. But I am now trying to share this media with Plex (any tips Kirk?) and some media will now need to be stored with a slightly different structure as Plex seems completely unable to make use of video files' embedded tags - talk about dumb. Anyway... I can of course place iTunes files wherever I want, as long as the aforementioned option is OFF, otherwise it will simply move everything back into its own structure as soon as that option is turned on. So I will need to keep it OFF if I am to keep those media files where I now want them to be (only a fraction of the total number of media files I have, but they now HAVE to be named differently). However, what are the ramifications of having that option off? If I drag any files into iTunes' window, presumably they are no longer copied or moved anywhere and just stay where they are. But what about anything dragged into the 'Automatically Add to iTunes' folder? They cannot really be left there, or are they? What does iTunes do? Does it in this case act as if that option is actually ON and move the files into the appropriate locations? Does it move them somewhere else entirely? What does it do? Any other ideas on how to keep the iTunes media folder organised, except for some files stored elsewhere? Or any other tips for sharing iTunes media with Plex?