For anyone else who encounters this, I found the issue. It actually was the AjaxControlToolkit. Apparently, the newest release does not dispose of controls properly when you have a modalpopupextender inside of an update panel. As a result, multiple controls of the same ID get created on the page. This caused me a whole lot of pain. This error turned out to be only the tip of the ice burg. Once I rolled back to an earlier version of the toolkit, all my problems went away.
Thanks.