November 2001: The UPnP patch debacle
Microsoft introduced Windows automatic updating as one of the great new benefits in Windows Me, around September 2000. A year later, we were treated to a Keystone Kops episode in the guise of MS01-059 -- ostensibly, a patch to the Windows Universal Plug 'n Play subsystem that prevented a buffer overrun. In fact, I think it was the first (though hardly the last) security bulletin conceived and scripted by Comedy Central.
Microsoft patched, repatched, and re-repatched the patch. The FBI's National Infrastructure Protection Center followed along like a kid cleaning up after his dog: NIPC issued a warning about the security hole, an update, another update, and ultimately an advisory that Microsoft had finally solved the problem.