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Helpful answers
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Aug 15, 2016 11:33 AM in response to jeskeneby roaminggnome,What will not play?
Please explain.
What did you transfer?You need to download iTunes on your mac, then transfer the iTunes library from your Windows machine.
How to move your iTunes library to a new computer - Apple Support
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Aug 15, 2016 11:35 AM in response to jeskeneby Christopher Lim,Could you please specify what part of iTunes you copied? Note: you do not need to copy the iTunes App to Mac. macOS runs .app programs while Windows runs .exe programs. Trying to run an .exe on macOS will result in finder saying there is no program to read this file and suggesting finding an App off of the App Store. If you simply want to copy your iTunes Media, check out this support page here.
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Aug 15, 2016 3:04 PM in response to jeskeneby Limnos,"iTunes" is the application only. It is not playable. it does the playing.
If these are Windows Media files those cannot be played by Mac iTunes.