The security of Microsoft products has been the target of jokes in IT and infosec for years, whether Justified or not. While Microsoft is the Publisher of modern products that do have significant security properties, how fast are old devices and software going the way of Clippy? Is your Source actually Safe? We'll take a look at the data that Duo Security has about the state of Exchanging new versions of software for old, Plus! we'll have enough puns to Sway your opinion toward "everything is not entirely awful".