We are coming up on the 30th anniversary of Windows 95. Windows 95 still didn’t make PCs as user friendly as Macintoshes of the day, but it was the first version of Windows that was good enough. Previous versions of the OS were terrible, and not just terrible in hindsight. Windows 1.0 all the way to Windows 3.1 were each terrible in their day. There is no better evidence of this than Windows 95 itself, an upgrade literally celebrated on the day of its release specifically because it heralded a clean break from a decade of mediocre releases. Here’s what I concluded on its 25th anniversary.
While modern day macOS has its roots in the original Macintosh System and NeXTSTEP, modern day Windows has its roots in Windows 95. Everything prior has largely been thrown away because even Microsoft knew it was garbage.
This may seem like mean spirited hyperbole to anyone who wasn’t around or aware during that era, but you don’t have to take my word for it. Go play around with Windows 3.1 right now on PCjs. It’s not good. Early versions of Windows are neat as a retro tech curiosity in large part because they are so unlike the modern versions used today. Now go check out Windows 95. While rudimentary, it’s still easily recognizable because every subsequent version of Windows was an iteration on what Windows 95 started.
iPad enthusiasts are excited by iPadOS 26 the same way PC enthusiasts were excited about Windows 95 for mostly the same reason. While iPadOS itself has been fine, its multitasking has been terrible. Like Windows 3.1, iPadOS’s various mechanisms for multitasking were all manageable, even useful in some cases, but they were never good. Like Windows 95, multitasking in iPadOS 26 is celebrated because it’s a fundamental departure from its predecessors. The similarities don’t stop there. Both Windows 95’s much improved usability and iPadOS 26’s much improved multitasking largely come from copying the Mac. Windows 95 embraced the Mac’s desktop metaphor with Mac-like window management and a more Finder-like Windows Explorer. iPadOS 26 embraces the Mac’s desktop metaphor, with Mac-like window management, and a more Finder-like Files app… oh and also there’s a menu bar.
Why Microsoft took a decade to decide to just copy the Macintosh is obvious — severe technical limitations of 80s era PC hardware and legal threats from Apple. Why Apple took a decade to just copy macOS for iPadOS multitasking is more of a mystery. iPads in 2015 were much more constrained hardware-wise, but I think that’s only part of the story. There is little doubt that Apple sees the iPad as an anti-computer of sorts. A device that does the stuff most people use computers for, but without the hassle and cruft. I wonder how much of Apple’s years long consternation about adding macOS style UX to iPadOS stems from a fear that the desktop metaphor itself was a cause of that undesired cruft. How can the iPad be the anti-computer if it looks just like a computer? Beyond embracing Mac-like features, I think the philosophical departure iPadOS 26 represents is a belief that traditional computers are complex for many reasons that have nothing to do with their interfaces. The iPad can have proper windowing, file management, a menu bar, etc… and still be the anti-computer so long as it continues to strictly manage or eliminate the undesired cruft of legacy computers. I love that large background tasks involve live activities and have to be user initiated. I’m sure some wish apps could run in the background a la macOS and Windows, but I would argue arbitrary backgrounding is exactly the sort of thing that makes those platforms complicated in ways that aren’t worth the squeeze for most users.
For the first time ever, multitasking in iPadOS 26 feels like something Apple can iterate on for decades, the same way they’ve done with macOS since System 1 and the same way Microsoft’s done since Windows 95. Just as nerds like me today look back at early versions of Windows as a weird era before Microsoft finally figured out desktop computing, future nerds will one day look back at early versions of Split-Screen, Slide Over, and Stage Manager as part of that weird era before Apple finally figured out iPad multitasking.