Can't sync some podcast episodes

Certain podcast episodes will not sync to my 5th generation iPod. My iPod was setup to sync automatically and the podcasts were setup to sync all episodes of all podcasts, but there are 4 or 5 episodes that will not sync to my iPod. Other episodes of the same podcasts do sync properly. I changed the settings to manually manage my iPod, but when I dragged these podcast episodes from my iTunes podcast folder to the iPod icon the + sign never appears and if I try to drop the episode into the iPod's podcast folder it still refuses to copy. What's broken?
Powerbook G4   Mac OS X (10.4.9)  

The files might be corrupted. Have you tried downloading again?

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