Originally Posted by Donatus
No. The songs that would not transfer were all purchased through iTunes.
Ah, hence my confusion - mine were purchased directly to my Mac.
OK, if Scootmein or another with the same experience doesn't answer first, I'll be looking for another solution for you.
Last questions - Windows, OS X or Linux? If not Linux, are you using iTunes on your PC?
Edit (posts merged) -
Okay, I remembered doing this sort of thing a few years ago on my iPod.
See, including the comments -
I think I used that one, can't recall for certain.
If the problem persists once it's all on your PC, see my earlier advice for transcoding to MP3 files.
Both are good for Mac or Windows.