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I set iTunes to "Keep iTunes Media folder organized" and to "Copy files to iTunes Media folder when adding to library" because I prefer to keep my music consolidated, organized, and consistent. However, when I have MP3s that are external to iTunes, then try to add via File > Add Folder to Libary, iTunes creates 2 copies of the file in the iTunes folder - one with the original song name and another with the original song name followed by the number 1.

Here is what I thought would happen, and I hope is possible:
1) Click File > Add Folder to Library
2) Select folder external to iTunes
3) Click OK
4) iTunes creates a clean new folder in the iTunes Music directory with exactly 1 of each file
5) Only 1 of each song is shown within iTunes

Is this too much to ask?

I am not an iTunes fan at all after 2 years dealing with the poor programming of this application. I hope someone can help me find the faith...

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if you're not a fan, why don't you just ditch this abomination? ;) – Molly7244 Dec 10 '09 at 4:06
Actually I've thought about it. But is there an alternative that will make it easy to download my podcasts and load them onto my iPod? Unfortunately the iTunes Store makes this all too easy (and I only get the free ones). – NoCatharsis Dec 10 '09 at 4:11
I use iTunes because I kind of have to, but prefer Media Monkey to manage my library. So I simply import every now and then the library kept organized by Media Monkey. Latest version 3.2 adds support for iPods, didn't get a chance to give it a try yet – Zoran Dec 10 '09 at 4:57
up vote 7 down vote accepted

iTunes does suck big time when it comes to keeping one's library organized (IMHO).

I uncheck the "Keep iTunes media folder organized" and also unceck "Copy files to iTunes Media folder when adding to library". That way, iTunes makes only one copy, and all files end up in one folder...

I keep my music organized via Media Monkey (, and import it every now and then in iTunes (which makes one copy of the files, and I don't care if they are organized or not there...).

That's the best solution I found... I make Media Monkey keep my music organized in folders Genre/Artist/Song (songs move when/if I change their genre), and I edit the tags etc in Media Monkey. Then, I keep importing the same folder in iTunes - it's smart enough not to import twice the same song, even if it moves around. You do get an extra copy of your music in iTunes' folder, but I don't mind... I view it as a temp folder...

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The culprit is likely the .m3u file. Either delete the .m3u file first, or select only the .m3u file (to preserve track order) and not the .mp3 files when adding to library. Adding both the .mp3 files as well as the .m3u file makes itunes create 2 copies of each song.

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The secret is to never check "Keep iTunes Media folder organized". I don't like softwares messing up with my collection. I set a folder in my machine (Like the default "Music" in Windows Vista) and put everything there in the structure that I'm used to.

Then, I use a third party plugin, called iTunes Library Updater, that searches these folders and add the files to my library. This way nothing is messed up, because it searches for the id3 tags and keeps my folder structure intact.

I don't like iTunes that much, is a memory hog for something simple. But everytime I try to use other application to sync with my iPod, something always go wrong, and I don't have time to configure everything myself. Doing the setup I described I have the best of both worlds (podcasts ease of use with iTunes with my own folder structure).

I'm using the iTunes Library Updater with my iTunes last version (9+).

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protected by Journeyman Geek May 29 '13 at 0:46

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