Problem with Itunes and transferring some songs to Ipod.

I recently encountered a problem in itunes when trying to transfer over 3 certain albums. Itunes can play these files just fine, but when I try to drag them over to my ipod it says that the song cannot be played on the ipod. The part that confuses me is that, I see no noticeable difference between this song and any of my others that copied over just fine. Here a screenshot(in spoiler).

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I opened up some details of both a song that wont transfer and a song that will transfer. There are noticable differences but both are .mp3 and should be transferrable.

I got more detailed specs on each song but I cant find the problem.(pictures blow. )

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by the looks of it, the first one isn't MP3, it's MP2. Try rencoding it.

by the looks of it, the first one isn't MP3, it's MP2. Try rencoding it.

Know of any free programs, to do that with?

I have no idea why, but I do know the problem. If a song ever has a short summary like the one in that 2nd pic in the comparison pic, it just causes a lot of problems. I dunno why, but that's what I've encountered. If a song has that full summary (like the 1st in the compare), then it works.

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If I had to guess I'd say you got these songs from Limewire? Garbage programs like that is the only place I ever ran into this problem. You have to pick better downloads, and if you get one with that really short summary, just delete it and get a better one.

That's the best fix I can offer. It's just so much easier to look around for a better download than converting. Unless this is like a really rare song or something... And there's better ways to get music than LM and similar crap programs, anyway.

Well, a quick fix would be right clicking on the track in iTunes and selecting the "Create ACC version" that should fix the can't-upload-to-ipod problem.