I feel really dumb, but somehow in the last 6 months, I couldn't figure out how to copy an AAC file that I purchased on iTunes to my iPod.
What I have tried:
- Dragging a file from “Purchased Music” to the iPod doesn' t work. When I drag the song over the iPod, it doesn't highlight the destination folder like it does in other folder playlists I have. It works for mp3 files, however.
- Dragging the filesystem folder over my iPod folder works, but it doesn't add any of the songs within it if they are AAC files.
- I thought maybe it wouldn't allow files I purchased from another computer, but I just bought two songs on that computer and it won't allow me to copy those either.
- My iTunes settings allow me to “Manually manage songs and playlists. I won't use the automatic as it severly messes up files that don't have proper tags.
- At the iTunes Support website there is a link to “Songs from iTunes Music Store do not copy to your iPod”, but the link is broken.
- Looking in the Apple Knowledge Base, I found an article called iPod troubleshooting basics and service FAQ that says I may need a new iPod version.
- I downloaded the iPod Updater, and it confirmed I needed a new version.
Bingo. Files were able to be copied.
It's the silly things that get ya sometimes…