ITunes videos won't play when artwork is changed

I have some of my own Quicktime videos that I've imported into iTunes (10.1.2) and they play fine. However, when I change the artwork to something custom (like a jpg of a screencap) the file will no longer play within iTunes. My Macbook Pro still plays it from Finder, and it works fine on my iPad, but not on iTunes.
To add insult to injury, if I then delete the artwork, it still won't play. It's like the file itself has become corrupted. I have to reimport it all over again from another source.

Found another problem. If I playback the file in iTunes, pause it, then right-click and hit "Set Poster Frame," the file also gets locked up. Plus it never actually changes the poster frame / artwork.

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