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I just put a bunch of songs on my iPod, and most of them worked. But now there’s two more that I need to download and when I drag and drop the files to the "Music" section of my iPod, the songs show up there, but they have that symbol next to them that suggests they are still syncing, and they are gray. But it's been like that for like three hours. So I know they are not actually syncing. Why is it doing this and how can I fix it?

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Have you tried syncing internally from iTunes? As in put the music into a playlist, and sync the whole playlist from the syncing tab? –  abc905 Jun 17 '12 at 0:35

2 Answers 2

You can also uncheck the songs in iTunes, sync with whatever device you are using, then recheck the songs in iTunes and sync again. Worked for me.

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Do you need to have "only sync checked songs" selected or de-selected for this? My guess would be the former. –  bmike Nov 20 '12 at 2:46

Some media cannot be played by the iPod even if the format is already AAC (.m4a in Finder). I've experienced this with media that was not directly purchased in the iTunes store. This broke the syncing and I ended up calling Apple Care Support.

What worked in the end was to convert all songs that were not purchased directly in iTunes to AAC using iTunes (right-click menu).

Then update your lists and try to sync them to the iPod again.

enter image description here

You really need to make sure that you have the right songs in the lists. Because I now had two AAC versions of the same song, I had to make sure that I only keep the version that iTunes created:

  1. Select the song
  2. Press +I (Get Info)
  3. Go to the tab summary and confirm that Encoded with says iTunes 10.X

enter image description here

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