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How do I sync iTunes library files (xml, itl) and music files/folders between these two different operating systems with different folder structures? I currently keep both the library files and the music files/folders in Dropbox, but every time I switch operating systems, I end up with half of my songs "missing" and the other 50% fine.

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Can you mount your windows drive in mac and vice versa? –  Jakob Weisblat Jul 23 '12 at 2:35
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2 Answers

Assuming Dropbox is installed on both computers, you should be able to move your iTunes library into your Dropbox, and then open it in iTunes on each computer. To do this on Windows, hold Shift while opening iTunes. On Mac, hold Option. Then, click on Choose Library and browse for the XML file.

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I'm guessing here. If you can try this and let me know the results:

  1. Log in to your Mac.
  2. Use iTunes.
  3. Play a short list (say ten or fifteen songs).
  4. Give Dropbox a huge amount of time to update (think an hour or more). Check to MAKE SURE that DropBox is done updating.
  5. Log out of your Mac when this is done.
  6. Log in to Windows, and DO NOT start iTunes yet. Give Dropbox a huge amount of time to update. Think an hour or more. I'm GUESSING that the database is updating when iTunes makes a call to try to use it.
  7. Try iTunes and post if there is any difference in the behavior.

If you're wondering, playing music causes changes in the database (update to play count among other things). I suspect that the WHOLE database has to re-download to sync. Let me know if this helps.

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