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40 free Microsoft Windows trivia questions with answers — trivia quiz, new questions added Aug 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 40 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 40 questions with answers and explanations. Play the quiz
Q 01Which Friends actor joined Jennifer Aniston in the 30-minute "cyber sitcom" video guide that shipped with Windows 95?
Matthew Perry
Matthew Perry's sitcom tour arrived with a genuine hit: Windows 95 shipped one million copies worldwide in just four days.
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 in January 1996 near the Napa–Sonoma county line, on a hill cleared of its vines by a phylloxera infestation years earlier.
Q 03Which ambient musician composed "The Microsoft Sound", the six-second start-up chime of Windows 95, in 1994?
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 four colours of the Windows logo to celebrate the Windows 95 launch?
Empire State Building
The Empire State Building had company in Canada, where a 100-metre Windows 95 banner was hung down the side of Toronto's CN Tower.
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 naming the 2015 successor to Windows 8.1?
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 practice was the cover story: Microsoft said the game was there "to soothe people intimidated by the operating system".
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 on the first consumer Windows not built on the Windows 95 kernel, uniting the home and business lines on Windows NT.
Q 10Which Windows 10 voice assistant took its name, and its US voice, from an AI character in Microsoft's Halo games?
Cortana
Cortana's US voice was Jen Taylor, the actress who had voiced the Halo character since the games began, while the UK version used Ginnie Watson.
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 with Windows 95 alongside the new Windows Explorer, as a place to review deleted files and folders before they are gone for good.
Q 13Which browser debuted as the new default in Windows 10 in 2015, pushing Internet Explorer into maintenance mode?
Microsoft Edge
Q 21Windows 1.0 was mocked for one layout rule that Windows 2.0 scrapped in 1987: what could its panes not do?
Overlap one another
Overlap one another was exactly what Apple objected to: the overlapping look in Windows 2.0 triggered its 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 torn down and rebuilt on Google's open-source Chromium engine from late 2018, 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 its buttons to which position by default, a first in the history of the operating system?
The centre
The centre-aligned bar is also pinned to the bottom of the screen for good; unlike earlier versions it cannot be dragged to another side without editing the registry.
Q 16Windows 10's revived Start menu bolted which feature of its tile-based predecessor onto the classic list of programs?
Live tiles
Live tiles sat on the right of a menu modelled on Windows 7's, a compromise Terry Myerson first showed at Microsoft's Build conference before the name was even announced.
Q 17What did the 2012 redesign of the blue screen of death add that was left out of Japanese and Windows Server editions?
A sad-face emoticon
A sad-face emoticon was joined in 2016 by a QR code, added to Windows 10 so users could scan their way to a troubleshooting page.
Q 18Which browser lost the 1995–2001 "first browser war" once Microsoft bundled Internet Explorer free with Windows?
Netscape Navigator
Netscape Navigator had dominated 1995, 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 so unloved that PC World renamed it the "Mistake Edition" and ranked it fourth among the worst tech products of all time.
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 helped make Windows 7 Microsoft's fastest-selling operating system, with more than 100 million copies sold in its first six months.
User Account Control's incessant prompts topped the list of Vista complaints, alongside driver incompatibility and its steep hardware demands.
Q 24What was the name of Windows XP's default blue-and-green visual theme, which some users dismissed as childish?
Luna
Luna had an exclusive sibling, the Royale theme, which was reserved for Windows XP Media Center Edition.
Q 25Internet Explorer 1.0 was sold in 1995 not inside Windows 95 itself but in which separate add-on pack?
Microsoft Plus!
Microsoft Plus! was pitched mainly on its themes and disk compression, so most people first met the browser preinstalled by PC makers rather than in a shop.
Q 26Which band's "Buddy Holly" music video was included among the "Fun Stuff" on the Windows 95 CD-ROM?
Weezer
Weezer shared the disc with Edie Brickell's "Good Times", a trailer for the film Rob Roy and the 3D bumper-car game Hover!
Q 27Which board game shipped with Windows 1.0 in 1985 after plans for Chess and a puzzle title were scrapped?
Reversi
Reversi sat alongside Calculator, Paintbrush, Notepad, Write and Clock in a package that sold for US$99 at launch.
Q 28Which scalable font format, developed by Apple, did Windows 3.1 adopt in 1992 as a rival to Adobe Type Manager?
TrueType
TrueType was Apple's late-1980s answer to Adobe's Type 1 PostScript fonts, and Microsoft's adoption made it the default on both platforms.
Q 29Which roll-back feature, letting a PC be returned to an earlier snapshot of its files, made its debut in Windows Me?
System Restore
System Restore shipped with a date-stamping bug that could mislabel any snapshot taken after September 8, 2001.
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 client reached US users on February 15, 2022, riding on the new Windows Subsystem for Android.