Adding artwork loops the audio

So after pasting in album artwork I notice it doesn't take to all files and if i try to paste to those files on their own it messes up the audio
i.e. a song will play the first 7 seconds and then start again so 1-7 and 8-15 are the same and the final 7 seconds of the song will be missing
I noticed this happening on my last PC and chalked it up to it being old but I've gotten a new PC with Windows 7 and I'm experiencing the same problem
Any help?

Yes. Assuming your iPod is set to manually manage the songs, connect the iPod, click on an album name in the browser (or a song name in the main window) and copy/paste a picture into the artwork box.
You can't add artwork directly to the iPod using the iTunes "add album artwork" feature this way though.

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