Problems Copying AAC Files to iPod

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:

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
  7. 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…

One thought on “Problems Copying AAC Files to iPod”

  1. Thank you so much for this quick description. I was facing the same problem yesterday. I just didn’t know what to do since the link from Apple’s site is broken.

    As you say, it’s the silly things that get ya sometimes.

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