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When you sign up with your Apple Account, you can provide valuable feedback to other community members by upvoting helpful replies and User Tips.
I have gone into the library, selected downloaded, then manually clicked on the song and move to device (my iPod). When I check the iPod, the songs aren't there and there's no indication that anything is happening.
Windows, Windows 10
I've done that. I can't just sync because I have music on my iPod that I downloaded directly to my old PC from the CDs, and if I do an autosync that will all be removed, so I have to do it manually, but the method in Apple Support isn't working.
Move downloaded songs from PC to iPod
