Q: I have many Audible books that I store on a NAS box. Each of my two Windows computers has iTunes installed and I have added all the books to the iTunes library manually. I put all the books in a directory called “AudibleBooks” on the NAS, however iTunes created a new sub-directory called “Audiobooks” and then several sub-directories under this for each author’s name when I clicked to organise the media folder. I’m happy enough with that, but as soon as I played the first book in iTunes I found a sub directory in “Audiobooks” called “Audiobooks” and a sub directory under that of the authors name of the book I had just finished. Now whenever I listen to a book the file moves from the original “Audiobooks/Author” to the “Audiobooks/Audiobooks/Author” directory. iTunes’ preferences shows the media folder as “Y:AudibleBooks” on the two PC’s I have with iTunes. I really don’t want this happening as iTunes loses track of books that moved. Is this expected behaviour? Can I stop it somehow? Am I drinking too much coffee and just imagining it?
A: It sounds like there’s a bug here somewhere, as this is definitely not expected behaviour for iTunes. The initial Audiobooks directory organized into sub-directories by author is completely normal, as the iTunes Media folder structure uses a top-level folder structure for each category of content. Since it sounds like all you have in this folder are Audiobooks, you would only get the single Audiobooks folder appearing here, but if you also had other types of content such as music and movies you would see additional folders alongside the Audiobooks folder for each of these types of content.
Once organized, however, there is no reason that iTunes should be moving these files a second time further down in the file system, and it is even more unusual for iTunes to be losing track of these files if it is in fact the one moving them in the first place. It is likely that how you’re mapping to your NAS device may have some impact this as well—if Y: is mapped directly to the “AudibleBooks” folder rather than the parent folder, then of course “Y:AudibleBooks” would actually be AudibleBooksAudibleBooks. Further, since you’re using two separate computers with the same NAS device, it’s also important to make sure that the Y: drive mapping and the iTunes Media folder path is set to the same values on both machines. Keep in mind that even if you’re storing the iTunes library database on the NAS device and referencing it from there, each computer still maintains its own separate iTunes preferences, including the iTunes Media folder location setting.
To help avoid issues like this NAS mappings should normally be done directly to the root folder of the NAS device with the iTunes Media folder configured as a full path from that point. In other words, if you have a “Media” folder at the root of your NAS device, and an AudibleBooks folder below that, your Y: drive should be mapped to the root of the NAS device and then the iTunes Media folder path should be set as “Y:MediaAudibleBooks” rather than mapping Y: to the “Media” folder and then trying to use “Y:AudibleBooks” as your iTunes Media folder.
When working with a network share and multiple iTunes libraries it’s often a good idea to simply disable the Keep iTunes Media folder organized setting in iTunes’ preferences, which will prevent iTunes from reorganizing your files behind the scenes.
This is especially important if you are using separate, locally stored iTunes library databases and only the content is on the NAS, since if one copy of iTunes moves your files somewhere else, the other copy will definitely lose track of this since it still expects the files to be in their original location. While using a common library database stored on the NAS is one way of dealing with this, it is not recommended as iTunes is not designed for multi-user access to the same database file, and database corruption can occur.