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Organize the iTunes folder in Finder with iTunes 9 Apps
Prior to iTunes 9, the iTunes folder structure in Finder had your movies, TV shows, etc. folders buried amongst the music. iTunes 9 allows you to enable sorting such that these all appear at the root of the iTunes Music folder. (That is, open your iTunes Music folder and you will now see folders for Audiobooks, iPod Games, Mobile Apps, Movies, TV Shows, Music, Ringtones, Voice Memos, etc.).

Please note that iTunes will reorganize your files, and you may find some orphaned folders that didn't quite fit into iTunes' organization scheme (it may also add a string of leading numbers to a music file's name in some instances).

Go to File » Library » Organize Library, and then click the Upgrade to iTunes Media organization check box. Once you've done this once, you won't have to do it again (and, in fact, the option will be grayed out).

[robg adds: Note that if you do this -- which I've done and recommend -- it will cause your next music backup (via Time Machine or other backup app) to potentially take a long time, especially if you have a large iTunes collection. In my case, it led to a 67GB Time Machine backup on the next run.]
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Organize the iTunes folder in Finder with iTunes 9 | 17 comments | Create New Account
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Organize the iTunes folder in Finder with iTunes 9
Authored by: saxphile on Fri, Sep 11 2009 at 8:25AM PDT
I tried the feature but it did absolutely nothing to my iTunes folder. It looks exactly the same as it did before, but now the option has been grayed out and I don't really know what else I can do.

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Organize the iTunes folder in Finder with iTunes 9
Authored by: kiltbear on Fri, Sep 11 2009 at 1:37PM PDT
Ditto (mostly). It moved SOME things but not all of them.

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Try looking inside the "Music/iTunes/iTunes Music" folder.
Authored by: iRideSnow on Fri, Sep 11 2009 at 3:00PM PDT
That's where you'll see the reorganized folder structure.

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Organize the iTunes folder in Finder with iTunes 9
Authored by: JazzDude on Fri, Sep 11 2009 at 3:41PM PDT
I had thought that, too. But all the folders now just contained orphaned .jpg, .txt and, most importantly, .pdf files which I then had to manually re-add (well, at least the .pdfs) to the respective music folders. These of course live now in a folder called "Music".

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Organize the iTunes folder in Finder with iTunes 9
Authored by: saxphile on Fri, Sep 11 2009 at 4:35PM PDT
You're right, it was all just jpg files (checked with grep for mp3 and m4a). For some reasons, all my PDF files did end up in the right places, but only Apple-supplied ones showed up in iTunes.

For the record, there were 350 freaking folders left and I only had 500 albums. I was expecting some stuff to be left behind from others' comments, but not this much.

For people who have the same problem as me, I think it's okay to junk those folders. Be careful you don't erase the vital folders now actually holding your stuff though. They are:

Audiobooks, Automatically Add to iTunes, iPod Games (only if you own a scroll wheel iPod), Music, Movies, Podcasts, and TV Shows. There are three more folders if you own an iPhone/iPod Touch: Mobile Applications, Ringtones, and Voice Memos.

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Organize the iTunes folder in Finder with iTunes 9
Authored by: joecab on Fri, Sep 11 2009 at 6:17PM PDT
I did it too but it only partially did it. I do see the new folders in there, but there's a bunch of stuff that it missed still sitting in there too.

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Organize the iTunes folder in Finder with iTunes 9
Authored by: joecab on Fri, Sep 11 2009 at 6:45PM PDT
Ah. On closer inspection, it just needed some manual cleanup. Here's what I found:

1. Empty folders that once contained songs. (The songs were found in their proper place in the Music folder.)

2. A number of songs that were zero bytes in size. (The originals were also found in the correct spot, except for one.)

3. A few songs that I thought I had renamed their albums. I renamed them again in iTunes and they popped back where they were supposed to go.

So I guess the process misses a few stragglers, but maybe two dozen songs to fix out of over 5,000 songs ain't bad.

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Organize the iTunes folder in Finder with iTunes 9
Authored by: kirsch on Fri, Sep 11 2009 at 8:41AM PDT
I read about this on TUAW and the author claimed that doing this causes Time Machine to back up all the files again.
If I understand correctly, due to the way HFS+ works, this wouldn't happen if the files are moved, so the statement makes me believe that the files get copied and then the originals deleted, as opposied to moved.

Can someone verify TUAW's claim?

I can survive Time Machine backing all my iTunes Library again, but I wouldn't want Backblaze to do it...

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Organize the iTunes folder in Finder with iTunes 9
Authored by: hibbers on Sat, Sep 12 2009 at 6:16PM PDT
I can survive Time Machine backing all my iTunes Library again, but I wouldn't want Backblaze to do it... It affected my Time Machine but Backblaze is fine and hasn't tried to re-upload anything (my library is 20 GB so I was also worried about this)

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Big overhead, no problem.
Authored by: revision29 on Fri, Sep 11 2009 at 8:54AM PDT
This is certainly worth reorganizing. It might even be worth going into Time Machine, selecting the day before the reorganization was done and using the tools toolbar button to delete all backups. This would remove the extra overhead from the re-backing up of the iTunes library, but would not give ability to recover stuff deleted prior to reorganizing.

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Organize the iTunes folder in Finder with iTunes 9
Authored by: dfbills on Fri, Sep 11 2009 at 9:46AM PDT
I think Rob is saying that TM does actually make another complete copy.

---
-d

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Organize the iTunes folder in Finder with iTunes 9
Authored by: teacy123 on Fri, Sep 11 2009 at 11:07PM PDT
Just make sure you back up your library BEFORE you use this function. When I executed it, it moved about 2/3 of my files into the new structure and left the other 1/3 in their original position. For those the references in the library got broken. Had to restore to a backup. Haven't tried again.


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Organize the iTunes folder in Finder with iTunes 9
Authored by: David Allen on Sat, Sep 12 2009 at 8:20PM PDT
It worked perfectly for me with a modest library of about 1000 songs, 35 movies, 20 subscribed podcasts, 50 TV Shows and 20 audiobooks. I ended with a folder with a song that was part of an album and an empty folder with an unfamiliar artist's name.

I put the song in the Automatically add to iTunes folder and it immediately filed the song correctly. Then I trashed the two empty folders.

---
David Austin Allen
Monterrey, NL, MX

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Organize the iTunes folder in Finder with iTunes 9
Authored by: teacy123 on Sun, Sep 13 2009 at 4:15AM PDT
I guess different folks have different definitions of perfect :-) From my perspective as a developer it is hard to screw up a couple of file move operations. And if they fail the operating system tells you, so you can tell the user. So whether it failed on 1000 or on 2 files, this is shoddy coding. I filed a bug report with Apple, let's see what it brings.


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Organize the iTunes folder in Finder with iTunes 9
Authored by: CarlRJ on Sun, Sep 13 2009 at 1:32PM PDT
I don't think it's bad coding, I suspect it's uncovering structural problems in user's iTunes collections (bad entries in the db, or disagreement between the db and the directory tree). It's moving the files associated with every track in your iTunes database (I'd be rather certain it isn't just moving the folders around wholesale), but if there's anything left over, well, what would you propose it do? Re-add the tracks? They might be duplicates; they might be corrupt; they might not be filetypes iTunes understands. It should, perhaps, put up a dialog saying that there were some things that it didn't know how to handle, and move those leftover folders into one top-level folder (though even that might be more confusion than it's worth, for the 90% of Mac users who don't pay attention to technical details on sites like this).

FWIW, I ended up with one extra empty folder, that was for an artist where I remember having done some odd file renaming directly in the filesystem. No other extra folders. I think the process is working as planned.

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Organize the iTunes folder in Finder with iTunes 9
Authored by: tooki on Fri, Sep 18 2009 at 5:56PM PDT
67GB? I laugh! After reorganizing, Time Machine had to back up my 785GB of media again. (5GB are music, the rest TV shows, thanks to EyeTV and iTunes Store.)

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Organize the iTunes folder in Finder with iTunes 9
Authored by: Targuman on Fri, Oct 9 2009 at 9:50AM PDT
Unfortunately I have far more than a few orphans. I have over 650 folders! Many with a single song each since they are from the free Apple Samplers available on facebook.

I cannot redo the organization and now I am not sure how to clean it up...What a mess.

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