Today at work I've been developing something to automate part of my Windows malware analysis routine (so many malware for Windows, one gotta automate it). Problem is the code isn't perfect, and malware causes many kinds of corner cases. So for every few hundred files, it crashes with the annoying Windows send/don't-send dialog (or the simple error reporting's OK/Cancel dialog).
When running this over thousands of files at a time, this could be really annoying, especially if I go and do something else in the mean while, so there's no one to close the dialog.
After digging around, I found this gem. A tool called ClickOff that automatically responds for dialogs, and can fill up forms, etc. I configured it to close the Windows error dialog, and now everything works smoothly without me having to watch over it.
I guess Windows operations weren't made to be script-ed or automated, so one has to use 3rd party tools to overcome this. Maybe this is why Administrators hate Windows.