Today, let’s take an even bigger step: copying your iTunes library. This is literally a drag-and-drop procedure, though it may take a little time.
Start by making sure you’re running the latest version of iTunes in your original version of Windows (XP or Vista). Then boot Windows 7 and install that same version. Any mixing and matching of old/new iTunes library files could lead to unpleasant results.
While still in Windows 7, exit iTunes, then click the Windows Explorer icon in your taskbar. (Wasn’t it nice of Microsoft to finally make Explorer so readily accessible?)
Browse into the Computer section, find your original Windows XP/Vista partition (on my system it was Drive D:, even though it appears as Drive C: when I boot to that partition), then navigate into the Users, Your Username, My Music, iTunes folder.
You should see various iTunes Library files and sub-folders. Now, find the corresponding iTunes folder in your Windows 7 partition, but don’t actually open it.
Instead, select all the files and folders from within the original partition’s iTunes folder, then drag them to the new partition’s iTunes folder.
Depending on how much music, video, apps, and the like you have, the copy process could take anywhere from a few minutes to an hour or more.
Along the way, Windows will likely notify you of a few duplicate files. Make sure to select the Copy and Replace option, as you want to overwrite the newer (and mostly empty) iTunes files with the ones from your original installation.
Once Windows has finished copying everything, start iTunes. Everything should be exactly as it was in XP or Vista. (One cool exception: When you mouse over the iTunes icon in the Windows 7 taskbar, you’ll see play/pause and skip controls you can use for music playback. No need to maximize the program!)
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