Keeping my iTunes "Music" folder in my DropBox
February 27, 2014 1:53 PM   Subscribe

I'm experiencing some problems with keeping my iTunes "Music" folder in my DropBox. Details (not too involved!) follow.

I'm using iTunes 11.15 in OS 10.8.5

A few months ago I moved my iTunes "Music" folder to DropBox. It's working....tracks there do play correctly when I choose them on iTunes.

1. When I download new music from iTUnes store, the song files all appear in /Users/Me/Music/iTunes/iTunes Media, dumped individually in that folder with no folder organization of any kind.

2. When I try to add music manually to iTunes (e.g. by dragging an mp3 file to iTunes), I get message "Attempting to copy to the disk Hard Drive failed. The required folder cannot be found."

1. I had put an alias (maybe it should be a symlink?) of my Music folder into /Users/Me/Music/iTunes/iTunes Media. I noticed this morning that the alias was broken, so I recreated it. Problem remains.

2. I noticed this morning that prefs/Advanced, "keep itunes media folder organized" was unchecked. I checked it, but problem remains.

3. I noticed this morning that prefs/Advanced, "Copy files to iTunes Media folder when adding to library" was unchecked. I checked it, but problem remains.
posted by Quisp Lover to Computers & Internet (6 answers total) 1 user marked this as a favorite
Response by poster: Sorry, that should read:
iTunes v11.1.5.
posted by Quisp Lover at 1:53 PM on February 27, 2014

Did you move it by using the "Change..." option under "iTunes Media folder location" on the Advanced tab of Preferences?
posted by Rock Steady at 2:15 PM on February 27, 2014

Response by poster: Don't remember. But, again, it's been working flawlessly for months. Aside from these two problems, which I've only just noticed.
posted by Quisp Lover at 2:22 PM on February 27, 2014

You could try putting the music back where it was, and make a symlink within the Dropbox folder. It sounds like iTunes and Dropbox don't quite cooperate, whether it's because of iTunes not liking the alias, or perhaps permission issues for Dropbox.

As a sketch, symlink creation would look something like
ln -s ~/Music/iTunes ~/Dropbox/iTunes
posted by Pronoiac at 12:30 AM on February 28, 2014

Response by poster: Went to an Apple Genius. He asked why I didn't keep the music files in my itunes folder and create a symlink to that in DropBox. I remember choosing to do it this way, but can't remember why.

So my move is to consolidate my entire library back to my hard drive, then symlink out the music files to dropbox.

Problem is I don't have enough drive space to duplicate all these files during the consolidation. SOOOO....I'm creating a new iTunes folder on an external drive, consolidating everything to THERE, deleting all my iTunes stuff from both dropbox and my mac's hard drive, then moving/consolidating itunes back to there. And THEN symlinking the music to dropbox.

Hours and hours and hours....
posted by Quisp Lover at 12:12 PM on February 28, 2014

iTunes is horribly implemented. You can't use a symlink or alias to your music folder. The pathname to each individual song is hardcoded. Use the iTunes option mentioned by Rock Steady to select the location and it might work better.
posted by alms at 5:31 PM on March 11, 2014

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