Q: I have a question about starting over from scratch with a new iTunes library for music. In addition, I want to make sure that my Apps and, to a lesser extent, some videos, ringtones and books, will be protected as well. Through the years I have had multiple computers, external hard drives and iTunes libraries. I have spent a good deal of time the last few weeks copying and getting all of my MP3s in one place, organized by artist in folders, on one external hard drive and I think I’m ready to take the plunge and purge my iTunes library and a few additional folder locations on my computer of copies of this music. However, I want to do it correctly because, I’m only part of the way done. I still have about 200-300 CDs that I want to import into my iTunes library to complete my collection and have all my music in one place. I want to avoid the problem of having multiple folders in multiple locations like I did before. I think that some of this came from the “Copy music to iTunes folder” box checked, so I will make sure that I have this unchecked when I eventually need to. However, what should I do now and how do I go about it correctly? For the time being, I will probably have all of my music on an external hard drive in one folder and have iTunes access it there. What do I have to do to make sure that my upcoming CD imports put the MP3s in the same location, organized into folders like I have it now? Also, what current folders on my Mac hard drive do I delete to get all of these extra copies of music off, freeing up space, after the transfer? And, finally, what do I do about my Apps, ringtones videos and books?

Reorganizing content into a new iTunes library

– Jim

A: While it sounds like you’re mostly on the right track, there are a few things that you should consider to make the transition smoother as well as setting yourself up to make things simpler should you want to relocate your library in the future.

Unless you have a compelling reason to organize your music into your own file and folder structure, such as accessing it with some application other than iTunes, it is strongly recommended that you actually let iTunes organize and manage your content for you. This not only eliminates any potential problems of the links in iTunes becoming broken if you decide to move your files around yourself, but will also make it much easier to relocate your library in the future, whether you decide to put it back on your Mac Mini’s internal hard drive or migrate it to a new external hard drive.

The key to setting this up is three options found in your iTunes Advanced Preferences: Your iTunes Media folder location and the Keep iTunes Media folder organized and Copy files to iTunes Media folder when adding to library options.

Reorganizing content into a new iTunes library

Ideally, you should set your “iTunes Media folder” location to a path on your external hard drive where you want to keep your music. In fact, you can set it to the path where your music is already stored. This is the path where iTunes will always place tracks that your import from audio CDs or download from the iTunes Store. Media files that you import from elsewhere on your computer will also be copied into this path if you have the Copy files to iTunes Media folder… option enabled.  If the Copy files… option is not enabled, then media files you import yourself are left where they are, and iTunes will reference them from those locations.

This behaviour of keeping the Copy files… option disabled may sound like the preferred approach to maintain your existing file and folder structure, but the problem with this is that iTunes will store the full path to each of your files in the external location and will never attempt to reorganize or manage those files, even when you want it to. This will prevent you from easily moving all of your content to a different drive in the future, since iTunes will continue looking for that content in the prior location. The only easy way to deal with this will be to use the Consolidate files option in iTunes to copy all of your music into an iTunes Media folder, which is essentially the same thing that the Copy files to iTunes Media folder… option does in the first place. In other words, if you ever plan to move your library to any other location, you might as well just store it in your iTunes Media folder now.

Note that you can avoid having iTunes make copies of your media files when you import them simply by setting the iTunes Media folder location to the path that already contains your media files. If the Keep iTunes Media folder organized option is enabled, then iTunes will reorganize all of your files into basically an ARTISTALBUM structure during import, but will move them rather than copying them, since they’re already in the iTunes Media folder. If the Keep iTunes Media folder organized option is disabled, iTunes will import the files without copying them and leave them as you’ve organized them, however you’ll likely end up needing to let iTunes reorganize them for you if you ever move to an external hard drive in the future.

Note that with iTunes 9 and later, the “iTunes Media” folder will also contain all of your other content, including videos, apps, ringtones and books. These are organized into their own sub-folders under the main “iTunes Media” folder. These other types of content can be imported into your new iTunes library in the same manner as MP3 files, and are handled in much the same way in terms of the copy and organization options—use the File, Add to Library option, or simply drag-and-drop the files or folders onto your iTunes window.


Reorganizing content into a new iTunes library

The other advantage of allowing iTunes to manage and consolidate all of your content is that as long as you had the Copy files… option enabled when you imported your content and haven’t changed your iTunes Media folder location, it’s safe to assume that any media files stored outside of your iTunes Media folder are not being used by iTunes. Note that you can also use the Consolidate files option found under Organize Library in the iTunes File, Library sub-menu to ensure everything is copied into your iTunes Media folder. See our article on Transferring your iTunes Library for more information on how the Consolidate Files option works and our Beginner’s Guide to iTunes for more general information on how files are stored within the iTunes library and how the various import options work.



Jesse Hollington was a Senior Editor at iLounge. He's written about Apple technology for nearly a decade and had been covering the industry since the early days of iLounge. In his role at iLounge, he provided daily news coverage, wrote and edited features and reviews, and was responsible for the overall quality of the site's content.