Q: I have iTunes set to automatically organize my music files in the iTunes Music Folder; however, I have noticed that iTunes truncates the file names if they are relatively long. I really don’t like this functionality. Is there a way to turn this off? And what would be the benefit in having the shorter file names?
A: Unfortunately, there isn’t any specific way to override this behavior, although where iTunes chooses to truncate the file name is somewhat dependent upon the underlying file system (ie, FAT32 or NTFS on Windows, FAT32 or HFS+ on Mac OS X). The file names are truncated in order to maintain compatibility with the file systems on both the computer running iTunes, as well as to ensure that they’ll be supported when transferred to the iPod itself.
The only option is to turn OFF the Keep iTunes Music folder organized setting in the iTunes advanced preferences and then pre-name your music files yourself prior to importing them into iTunes. Note that if you do this, you will also need to either turn OFF the Copy files to iTunes Music folder when adding to library setting in the same preference panel, or place the items to be imported in the iTunes Music Folder, otherwise iTunes will rename them as it copies them into its music library folder.
One other setting that might help if you wanted to continue allowing iTunes to organize your music would be to omit the track numbers from the front of the file names. This can be accomplished by UNchecking the Create file names with track number setting in the importing preferences.
While it may not make much of a difference, this will save you some space on the front-end of each file name, thus getting you two or three extra characters on the end of each file name.