I was working on a system that was suspected of being infested with malware. Sadly, it was clean - the flakiness was caused by all of the security utilities and software that had been installed on the system. But that's a rant for a different day. In the process of dealing with the system, an application crashed. I don't recall specifically what it was, but whilst gathering information about the crash, Dr. Watson had some problems himself. The good doctor just couldn't cope, apparently.
I love the standard wording: "DrWatson Postmortem Debugger has encountered a problem and needs to close. We are sorry for the inconvenience."
I think in this case I chose to send the error report to Microsoft. =8->