Most Epic Fail: http://pwnie-awards.org/2008/awards.html#fail
Gee . . . I hope we . . . win? No . . . wait . . .
Windows Vista for proving that security does not sell
$100,000,000 invested in security and what does Microsoft have to show for it? Customers are revolting against Windows Vista and nobody who has a choice is chosing to upgrade. It doesn't matter that Vista really is the most secure Microsoft operating system ever made, all customers care about is the annoyance of the UAC prompts, the confusing user interface and the insane hardware requirements.
The good thing about the Vista debacle is that no other vendor will care to do such a security push, which means that we'll be able to easily own any piece of software for the foreseeable future.