Microsoft Windows Trivia
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90 free Microsoft Windows trivia questions with answers — trivia quiz, new questions added Oct 2026.
Windows has been the world's default desktop for four decades, and its history is stranger than the corporate image suggests. There was a launch party that lit up a New York skyscraper, a start-up chime written on a rival's computer, a stage demo that crashed in front of the company's own founder, and a card game bundled mainly to teach people how to use a mouse. These 90 questions run from Windows 1.0 to Windows 11: codenames and release years, the Start button's arrival and brief disappearance, Solitaire and the other bundled games, the paperclip assistant, the blue screen of death, the browser wars and the crossovers with Microsoft's games console. Most are pitched for a pub table or an office quiz, with a final run for people who remember installing from floppy disks. Play on your phone with instant answers and explanations, or print it for a pub quiz, a classroom or an IT team's Friday afternoon.
30 of 90 questions with answers and explanations. Play the quiz
Q 01Which Friends actor joined Jennifer Aniston in the "cyber sitcom" video guide Microsoft released for Windows 95?
Matthew Perry
Matthew Perry's sitcom tour was one piece of a launch blitz for which Microsoft also paid millions to use the Rolling Stones' 'Start Me Up' as its theme song.
Q 02What is the name of Windows XP's default wallpaper, a photo of green hills under a blue sky in California?
Bliss
Bliss was shot on film one January, after winter rain had turned an unplanted hillside green; the slope has since been covered in vines, and the view is now barely recognisable.
Q 03Which ambient musician composed "The Microsoft Sound", the six-second start-up chime of Windows 95?
Brian Eno
Brian Eno later admitted on BBC Radio 4 that he composed the Windows chime on a rival machine: "I wrote it on a Mac."
Q 04Which New York landmark was lit up in the colours of the Windows logo to celebrate the Windows 95 launch?
Empire State Building
The Empire State Building was one stunt among many: in London, Microsoft paid for the entire 1.5 million print run of The Times and gave the paper away free.
Q 05Which Microsoft operating system of October 2012 was the first public release since 1995 to ship without a Start button?
Windows 8
Windows 8 treated the desktop as just another app, and the complaints were loud enough that Windows 8.1 put the Start button back a year later.
Q 06Which version number did Microsoft skip entirely when it named its 2015 release of Windows?
9
Windows 9 was passed over because, in Terry Myerson's words, "it wouldn't be right to call it Windows 9" given how different the product was.
Q 07Windows 3.0 bundled Solitaire in 1990 partly to teach nervous new users which mouse technique?
Drag and drop
Drag and drop was the lesson, and the teacher was an intern: Wes Cherry wrote Solitaire and gave it a boss key to hide the game on screen, which Microsoft made him remove.
Q 08Which puzzle game joined the standard Windows 3.1 install in 1992 after debuting in the Microsoft Entertainment Pack?
Minesweeper
Minesweeper hooked its own boss: Bill Gates was so addicted he used to sneak into a colleague's office after work to play.
Q 09The two-letter suffix of Windows XP, unveiled under that name in February 2001, was short for which word?
Experience
Experience was the marketing gloss; underneath, XP moved home users off the Windows 95 line and onto the NT core built for business, uniting the two families.
Q 10Which Microsoft assistant took its name from an AI character in the company's Halo games?
Cortana
Cortana was only meant to be an internal codename, but leaks and a fan petition persuaded Microsoft to keep the name for the finished assistant.
Q 11On which day of the week does Microsoft ship its monthly batch of Windows security fixes, a routine formalised in 2003?
Tuesday
Patch Tuesday falls on the second Tuesday of each month and was introduced in October 2003 to cut the cost of patching after the Blaster worm.
Q 12What did Windows 95 call its holding area for deleted files, a feature Apple's Macintosh had long known as the Trash?
Recycle Bin
The Recycle Bin arrived just after Apple's long lawsuit over lookalike desktops, which Apple lost on almost every point except a ruling that a rival's trash-can icon copied its own.
Q 13Which browser debuted as the new default in Windows 10 in 2015, pushing Internet Explorer into maintenance mode?
Microsoft Edge
Q 21Which ability, missing from Windows 1.0, did application windows gain when Windows 2.0 arrived in 1987?
Overlap one another
Overlap one another: Windows 1.0 could only tile its windows side by side, and the overlapping look of 2.0 prompted Apple's 1988 copyright lawsuit, which Microsoft won.
Q 22Plugging which device into a Windows 98 demo PC at COMDEX 1998 crashed it to a blue screen before Bill Gates?
A scanner
A scanner was meant to show off Plug and Play; Gates's reply to the crowd's applause was "That must be why we're not shipping Windows 98 yet."
Q 23Which Windows Vista security feature dims the whole screen and asks permission before an app may alter core settings?
User Account Control
Microsoft Edge was later torn down and rebuilt on Chromium, the engine project behind Google's rival Chrome, abandoning Microsoft's own EdgeHTML.
Q 14Which US city served as Microsoft's codename for Windows 95 while the 32-bit system was in development?
Chicago
Chicago ran in parallel with "Cairo", a planned Windows NT-based successor with an object-based file system that never shipped as such.
Q 15Windows 11's taskbar moved the Start button and app icons to which position by default?
The centre
The centre layout was salvaged from Windows 10X, a version of Windows planned for dual-screen devices that Microsoft cancelled before it ever shipped.
Q 16Windows 10's revived Start menu bolted which feature of the previous version's Start screen onto the classic list of programs?
Live tiles
Live tiles sat beside a Windows 7-style list as a compromise first shown in 2014, then vanished altogether when Windows 11 replaced them with a grid of plain icons.
Q 17What did the 2012 redesign of the blue screen of death add above its newly simplified error message?
A sad-face emoticon
A sad-face emoticon was joined in 2016 by a QR code linking to a troubleshooting page, but the blue itself was on borrowed time: in 2025 Microsoft announced the crash screen would turn black.
Q 18Which browser lost the 1995–2001 "first browser war" once Microsoft bundled Internet Explorer free with Windows?
Netscape Navigator
Netscape Navigator had dominated the mid-1990s, but free bundling let Internet Explorer reach a peak of about 95% usage share by 2003.
Q 19What did the "Me" in Windows Me, the last release built on the Windows 9x line, officially stand for?
Millennium Edition
Millennium Edition was dubbed the 'Mistake Edition' by PC World, which ranked it fourth among the worst tech products of all time after users struggled to install it, run it or even shut it down.
Q 20Which Windows 7 feature maximises a window dragged to the top of the screen, or docks it to half when dragged sideways?
Aero Snap
Aero Snap came from Microsoft's finding that lining up two windows side by side took a fiddly run of clicks, moves and resizing; Snap cut that to one easy motion per window.
User Account Control nagged by design: a Microsoft manager admitted it was built to 'annoy users' so that software makers would write safer programs, and Windows 7 toned the prompts down.
Q 24What was the name of Windows XP's default blue-and-green visual theme, which some users dismissed as childish?
Luna
Luna's bright colours got Windows XP mocked at launch as a 'Fisher-Price' or 'Teletubby' system, years before it became the Windows that users refused to give up.
Q 25Internet Explorer 1.0 went on sale in 1995 as part of which add-on pack, sold separately from Windows 95 itself?
Microsoft Plus!
Microsoft Plus! carried a browser built on code licensed from Spyglass; the two fell out over how much Microsoft owed in royalties, and Microsoft paid $8 million in 1997 to settle.
Q 26Which band's music video was included among the "Fun Stuff" on the Windows 95 CD-ROM?
Weezer
Weezer were not told that 'Buddy Holly' would be on the disc: their label made the deal with Microsoft without them, and drummer Pat Wilson recalled being furious about it.
Q 27Which board game shipped with Windows 1.0 in 1985 after plans for Chess and a puzzle title were scrapped?
Reversi
Reversi arrived in a Windows that was itself overdue: Microsoft announced it in 1983, then took two more years of repeated delays to get it out of the door.
Q 28Which scalable font format, developed by Apple, did Windows 3.1 adopt in 1992 as a rival to Adobe Type Manager?
TrueType
TrueType reached Windows through a swap: Apple, wary of paying Adobe royalties, licensed it to Microsoft in return for a PostScript clone called TrueImage, which Apple never put in a product.
Q 29Which roll-back feature made its debut in Windows Me?
System Restore
System Restore shipped with a date bug: checkpoints created after September 8, 2001 would not restore the computer until Microsoft issued a fix.
Q 30Windows 11 ran Android apps through a partnership with which company's app store, starting in the United States in 2022?
Amazon
Amazon's Appstore reached US users in February 2022, but the experiment was short-lived: Microsoft announced two years later that Android apps on Windows would lose support on 5 March 2025.