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Do both computers need to be running the same operating system for home sharing on iTunes? i.e. do both have to be windows or mac?

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No, I believe that Itunes itself installs the required components needed for home sharing.

If you are talking from Itunes on a Mac to Itunes on Windows, it should not be a problem.

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I would rather say that don't have to, but that it helps. –  harrymc Sep 18 '09 at 20:51

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