Move Your iTunes Library from Mac to Windows

I finally got around to transferring our music library from an old Macintosh (so old it’s a PowerPC) to our new Windows 8.1 system. It worked, but it wasn’t quite as smooth – or as automatic – as I’d hoped it would be.

In theory it’s easy: Copy the iTunes folder from the old system to the new one, whether over the network or using an external drive. Make sure you include the iTunes Library.itl file to keep your playlists, ratings, etc. And if your library is scattered around the drive, be sure to consolidate it first.

Problem 1: Different folder structure

This probably has more to do with which version of iTunes you started with than which platform, but the old system had all its songs in iTunes/Music and the new system had its small collection in iTunes/iTunes Media/Music. So I couldn’t just change the iTunes data folder and be done with it.

Another complication was with albums and artists that didn’t end up lining up correctly in the filesystem: Spamalot, for instance, had each singer listed per song, and one version of iTunes had split it across about 10 folders.

Problem 2: Illegal characters

The Mac version of iTunes will (or at least used to) use characters in filenames and directories that aren’t allowed on Windows, like question marks and quotation marks. Even after pointing it to the right folder, it was still missing about 70 songs, which I had to manually locate.

Fortunately, iTunes marked the songs that were missing with an exclamation mark in a circle next to the track number. Unfortunately, it wouldn’t sort or filter on it. That meant I needed to page through the entire library looking for those symbols.

Problem 3: iPod drivers/resync

You have to wipe and re-sync your old iPod. I was expecting this. The problem I had was that Windows set up the drivers…and then that was it. Neither iTunes nor Windows gave any indication that they knew the iPod was there, even though the iPod was showing its “Do not disconnect” message. Well, no indication until iTunes suddenly stopped responding entirely…

Finally I just unplugged the iPod (which rather upset the three-year-old, because it was telling us not to but we did it anyway!), at which point iTunes closed. But the system started responding again, and iTunes came right back up when I opened it. When I plugged it back in (after rebooting the iPod, just to be on the safe side), iTunes recognized it right away and offered to reformat it. It synced without any further complaints!