Q: How do I move a group of referenced songs in my iTunes Media Folder from one directory to another directory in the same media folder? Whenever I move them, iTunes keeps putting them back into the original directory. I’ve found that unchecking the “Keep iTunes Media folder organized” option works temporarily, but once I turn it back on, it moves the songs back. Any ideas?
A: The short answer is that you can’t really do this without disabling the “Keep iTunes Media folder organized” option entirely; the whole point of the setting is to do just what the option suggests — maintain your media files in iTunes’ standard file and folder structure.
That said, if you wish to organize your files — even a small handful of them — in your own way, there’s probably no need to have the option turned on at all. As long as the second option, “Copy files to iTunes Media folder…” is still enabled, anything you import into iTunes from outside of the iTunes folder will still be organized into the standard structure — it has to go somewhere — but files won’t be moved around once already inside the folder unless the “Keep iTunes Media folder organized” option is also enabled. This also means that if you copy files into your iTunes Media folder manually before you import them, iTunes will also leave them wherever you originally placed them. In other words, files added to your library from outside of the iTunes Media folder will be copied in and organized by iTunes, while files added to your library that are already in the iTunes Media folder will be left where they are.
Of course, turning this option off also means that files won’t get reorganized if you update their track info – they’ll simply be left wherever iTunes originally placed them when you first imported them, or wherever you placed them if you’ve moved them around manually. By default, the iTunes Media folder structure uses track information such as artist and album name to place files, and when the “Keep iTunes Media folder organized” option is enabled, it will move your tracks around as you update this information.
If you really want to leave the “Keep iTunes Media folder organized” option enabled, for whatever reason, then the only other alternatives are to either change the appropriate track information (e.g. artist and album) to tell iTunes to place the tracks elsewhere, or to move the files to a location outside of the iTunes Media folder with the “Copy files to iTunes Media folder…” option disabled, in which case the files will be left where they are and referenced from that location instead. Note that you can temporarily override the “Copy files” setting by holding down the OPT key (Mac) or ALT key (Windows) when dragging and dropping files into iTunes, which can be much faster than a trip to your iTunes Preferences when you only want to override this setting on an occasional basis.