Custom vs. standard iTunes file structure management


Q: For several years now I have been reluctant to let iTunes manage my music library, mainly because I dislike the system iTunes establishes for maintaining music files (for example, multiple album folders, truncated file names, and compilation folders). I carefully structured my own system for file nomenclature and management long before iTunes was made available for PC users, and I have been hesitant to surrender management to what I believe to be iTunes’ inflexible system. However, I pay a price. Every time I try to clear an unwanted file out of iTunes and delete it from my computer, I have to go manually delete the file using “Show Song File” first. I also have to work around the issue when importing music. Is there any option or trick that allows iTunes to manage your music library even when you use a system for file naming and organization that is different from the iTunes default?

– Wilson

A: Unfortunately, the short answer is “no.” There is simply no way to customize the “Manage my Music Library” function of iTunes, though several power users would surely like to be able to do so. 

The long “answer” is on the surface an evangelistic, persuasive anecdote: Before iTunes debuted on the PC, one of our editors exclusively used Winamp in conjunction with Tag&Rename to meticulously maintain filenames and ID3 tags, ensuring a logical file structure and complete synchronization of ID3 and filename information. When iTunes was released for the PC, this editor too was extremely skeptical of the “hands-off” approach that iTunes encourages as far as the file system is concerned. He made 3 redundant backups of his pristine MP3 collection, and allowed iTunes to do with the master as it pleased, giving “the iTunes way” a week trial. In that week, he never once regretted the switch. Never did he need to access the filesystem directly. When he needed to deal with a file directly, he simply dragged the song(s) out of the iTunes library window onto the Desktop (which makes a duplicate copy) and used that. When he needed to fix a tag, he did it in the same program that does burning, playback, and syncing.

We’re certainly not suggesting that everyone can or should adapt to iTunes management, but it is potentially enlightening, even for the most die-hard “custom nomenclature” fans. Try it, and you might be amazed at being able to enjoy your music rather than care for it.

Jerrod H. is an iLounge Contributing Editor, with frequent contributions to our iPod 101 and 201 tutorials, plus occasional hardware and software product reviews.
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Jerrod H.

Jerrod was a contributing editor at iLounge. He mostly wrote articles about iTunes and iPod accessories. He was known for his in-depth knowledge of both topics and was often able to provide readers with unique insights into the world of Apple products.