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I have an old MacBook on which I'm using iTunes to listen to my music. What is important to me is that I organize the folders and filenames of my music manually, i.e. I have the box "Keep iTunes Media folder organized" in the "Advanced" section of the iTunes Preferences unchecked.

(I know that at this point, many people will say "why don't you just let iTunes sort your music", but that's not an option for me. I don't want any software to handle the folder / file structure. Moreover, a sorting based on artist, album and track title is useless for sorting classical music, which is a very important part of my music collection.)

I just bought a new MacBook Air, but I will keep using my old MacBook. Now I want to have my music synced between the two Macs. I have all my music in a Dropbox folder, which will soon be completely downloaded to my new MacBook Air.

My question is: Is there a way to set things up such that I can manually add new music to the (Dropbox) music folder, with all tags set right, such that they will automatically be imported to both computers' libraries, but without "Keep iTunes Media folder organized" being checked? Or at least such that if I import it to iTunes once, it will automatically be imported to the iTunes library on the other computer?

I noticed one thing: The library files of the iTunes on my old MacBook are placed in ".../Music/iTunes/iTunes Music". Even if I choose a new location for the iTunes library, as long as I leave "Keep iTunes Media folder organized" unchecked, it doesn't move the library files to that new location. Thus, I don't know how to move the location of the library files to the Dropbox. Even if I would know, I'm not sure whether things would work because the Dropbox folder does not have the same full location string on the two computers because, for example, the home folders have different names.

Any ideas?

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You can put your entire iTunes library (not just the music files) into the Dropbox and create iTunes aliases in your ~/Music folder on both computers, as long as the paths are identical. This means you need to use the same user name on both machines. Ie., /Users/Username/Music/iTunes/iTunes Music. Then, when you add music to iTunes on one machine, when the library syncs over Dropbox, the music will be present on the other machine.

  • Is there a way to do the same when the paths (i.e. the usernames) are not identical? – Corsin Pfister Jan 29 '15 at 8:59
  • You could try faking a username and alias in your Users folder. sudo mkdir /Users/identical_username sudo mkdir /Users/identical_username/Music sudo mkdir /Users/identical_username/iTunes Then put your alias in there. This is a total guess tho. – selfagency Jan 30 '15 at 20:38

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