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Is it possible for me to keep my iTunes libraries in sync with each other on OS X and Windows if so how? My iTunes library is stored on a network share made available via AFP and SMB. Is it possible for me to make it so that any changes made on iTunes on Windows are also shown in OS X and vice-versa or will I have to maintain separate iTunes Libraries resulting in a clunky mess (especially when iTunes Match starts uploading playlists twice and other things)?

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See iTunes: Moving iTunes Files (Self Managed) for a better explanation of how to achieve dual, almost-in-sync libraries across different machines

[This is not a hugely technical explanation, more one of the frustration I've had doing the same thing... if you want more details, ask...]

You can share the file location, but both machines will 'see' it differently. iTunes uses absolute references [truly irritatingly] so the only way to keep the Library in sync is to either add the same files to both [not good if it's supposed to be self-organising] or to manually copy the iTunes Library.xml file & use BBEdit to change the path structure for every entry - which can be done but then may take the Windows version of iTunes up to 10 hours to process it.

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  • "which can be done but then may take the Windows version of iTunes up to 10 hours to process it." - No disrespect to Apple but the OS X version of iTunes is just as clunky :(. Where is the iTunes Library.xml file stored, is it in some temporary / hidden directory?
    – aidanharris
    Commented Aug 29, 2014 at 18:57
  • it's in 'Music' ... ~/Music/iTunes/iTunes Library.xml & yes, I'm pretty sure many of us wish the paths were relative ;-)
    – Tetsujin
    Commented Aug 29, 2014 at 19:11

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