Vintage Computing and Gaming shares a fourteen pages/slides Technologizer article showing "Windows Oddities: 25 Years of Microsoftian Weirdness -- Contrary to popular belief, Windows is far from boring. Dig below the surface, and you'll discover a stranger side to the world's most popular operating system. It's filled with twisted homages, forgotten platforms, and dead ends. In a word, it's full of oddities.
Neatorama shares "Damn You, Autocorrect!" (has cussings and not safe for work (NSFW)) -- "If you have an iPhone, iPod, or iPad, you know how annoying the Auto Correct feature can be. It changes words without rhyme or reason, and if you're chatting with someone and hit 'send' too quickly, it can really make you look like an idiot.
Vintage Computing and Gaming shares a twenty pages PC World slide show showing "a brief history of computer displays. From blinking lights and punch cards to liquid crystal displays (LCDs) and third dimension (3D) flat panels, we trace the 70-year history of the tech/technology that users rely on to see what a computer is doing...
This Savage Chickens comic strip shows why your overlord's keyboards are always dirty/filthy.
So Much Pun shows a photograph/photo. of real-life ctrl-
rationallyPARANOID has a list of commercial products that included malware since 2000.
This XKCD comic strip shows what your overlord and other computer people/geeks/nerds go through with support
This Dilbert comic strip shows why your overlord doesn't help with other people's computers