Songs of right file type won't work!

It's mostly with the songs I rip from CDs, even after I change them to an MP3 format. Sometimes it happens with songs I download (from Limewire) too.
It's not that they won't go from iTunes to my iPod, they won't even go on iTunes at all. When I tried opening the files in Windows Media Player, it said, "The file you are attempting to play has an extension that does not match the file format". Is this the problem? If it is, what do I do to solve it?

So, it seems as though you tried to change the file format by just changing the filename. If you're able to open them through iTunes, you'd be able to convert them to another type, if you can't, nor put them back to their original format you might have to re-import them all. I'd recommend Importing them through iTunes itself.

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