Microsoft Bob, Active Desktop, SideShow, Windows RT, and Windows 10X: five Windows projects that crashed and burned, yet their genetic code is scattered across every Windows 11 PC. The recently resurfaced catalog of these misadventures—as detailed by MakeUseOf—isn’t just a nostalgia trip. It’s a practical guide to understanding why your Start menu looks the way it does, when an ARM laptop makes sense, and what Widgets are actually trying to accomplish.

The experiments themselves are dead, but their lessons are alive in the Settings app, the taskbar, and the purchase decisions you face right now. Here’s what every Windows user should know.

What Actually Happened: The Quick Version

Between 1995 and 2021, Microsoft shipped—or at least announced—five major Windows experiments that all ended the same way: pulled, canceled, or quietly abandoned. Each tried to drag the PC into a future Microsoft saw clearly but couldn’t yet deliver.

  • Microsoft Bob (March 1995): A $99 cartoon overlay for Windows that turned the desktop into a house. Rover the dog offered help bubbles. It needed 8MB of RAM and a 486 processor, flopped within a year, but gave the world Comic Sans and later inspired the Windows XP search dog.
  • Active Desktop (1997, built into Windows 98): Let you display live webpages, stock tickers, and news directly on your wallpaper. It tied Internet Explorer 4 so deeply into Windows that it became part of the antitrust case. Fragile on dial-up, often crashed, but the idea of always-on glanceable info was sound.
  • Windows SideShow (Windows Vista, 2007): A platform for tiny auxiliary screens on laptop lids and keyboards. The Asus W5Fe had a 2.8-inch external display to check email without opening the laptop. Almost no hardware shipped, and Microsoft removed it in Windows 8.1.
  • Windows RT (October 2012, launched with Surface RT): A version of Windows 8 for ARM processors that looked like Windows, had a desktop, and included Office—but couldn’t run any traditional x86 desktop apps. It led to a $900 million inventory write-down in 2013.
  • Windows 10X (announced October 2019, canceled May 2021): A lightweight, modern Windows for dual-screen devices like the Surface Neo. Neither the OS nor the Neo ever shipped, but its centered taskbar, simplified Start, and rounded corners resurfaced in Windows 11 just weeks later.

What Each Failure Means for Windows Users Today

The practical fingerprints of these flops are all over your current PC. Understanding them helps you make smarter choices now—and recognize when Microsoft is trying the same idea again.

The ARM Question: When a Windows Laptop Isn’t Quite Windows

Windows RT’s collapse taught Microsoft a brutal lesson: Windows is its app library. The current generation of Snapdragon-powered Copilot+ PCs runs Windows 11 on ARM with full x86 and x64 emulation, meaning most of your existing software will install and run. Microsoft’s own documentation confirms that “many unmodified x86 and x64 applications” work through emulation, and x64 support specifically broadened with Windows 11.

But the ghost of RT lives in the fine print. Some peripherals still need ARM drivers, games with anti-cheat might fail, and specialized enterprise tools may choke. Before buying an ARM laptop, check your critical apps. If they rely on low-level drivers or custom installers, assume you need to test first. The Surface support page explicitly warns that “some peripherals may not install” without ARM-specific manufacturer software.

In short: Modern Windows on ARM is no longer RT, but it still isn’t a drop-in replacement for every x86 use case. The difference is that today Microsoft tells you that upfront.

Glanceable Info: From Wallpaper to Widgets to… Your Phone

Active Desktop and SideShow both tried to answer the same question: How do you see what matters without opening an app? Active Desktop put live content on the wallpaper; SideShow put it on a tiny external screen. Both failed because they added fragility and demanded hardware ecosystems that didn’t exist.

But the idea never died. Windows 11’s Widgets board is Active Desktop’s spiritual successor—a quick-access panel of news, weather, and calendar, now delivered through a secure, sandboxed container rather than raw HTML on your wallpaper. The key difference is that Widgets are more curated and less crash-prone, but they still share the same flaw: they pull you out of your workspace into a feed that can become a distraction machine.

Meanwhile, SideShow’s real heir is your smartphone. Its lock screen and your smartwatch deliver exactly the glanceable information SideShow promised—but on devices you already own. The lesson for Windows users: If you find Widgets feeding you more noise than signal, turn off the news feed in Widget settings. The feature is meant to surface what you need, not replicate a social media scroll.

The Friendly Interface Trap

Microsoft Bob’s cartoon house tried to make computing approachable but ended up condescending. Today’s AI assistants, Copilot suggestions, and even the Windows 11 Start menu walk a similar line. When Windows constantly nudges you with tips, suggested content, or AI write-ins, it risks the same user revolt Bob faced.

The practical rule: Customize. Windows 11 allows you to turn off suggestions in Start, lock screen, and taskbar. If you find the system infantilizing, those toggles exist for a reason. Microsoft learned from Bob that assistance must be opt-in, not a mandatory layer between you and your work.

The 10X Inheritance: Why Windows 11 Looks the Way It Does

Windows 10X never launched, but it’s the clearest example of a dead project donating its organs to a live one. Windows 11’s centered taskbar, simplified Start menu (no live tiles), rounded corners, and overall cleaner aesthetic are direct descendants of 10X. If you’ve ever wondered why Microsoft changed the taskbar alignment after decades of left-aligned icons, the answer sits in a canceled dual-screen OS from 2019.

This matters because 10X was designed for a world of touch-first, mobile productivity. Windows 11 inherited that DNA even on desktop machines, which is why some power users find the new taskbar and Start menu less efficient. The lesson: You can move the taskbar back to the left in Settings → Personalization → Taskbar. Windows 11’s design is a compromise between 10X’s vision and classic desktop reality.

How We Got Here: A Brief Timeline

Understanding the sequence reveals a pattern of Microsoft betting on upcoming trends—and repeatedly misjudging the hardware or ecosystem readiness.

  • 1995: Microsoft Bob launches at $99. Too heavy on resources, too patronizing. Discontinued within a year, but Comic Sans (designed for Bob, though not shipped with it) appears in Windows 95 Plus! and becomes a cultural token.
  • 1997: Active Desktop arrives in Internet Explorer 4, woven into Windows 98. The feature pushes live web content onto the desktop, but dial-up speeds and limited RAM make it more of a tech demo than a daily tool. It also fuels the antitrust fire: Microsoft argued IE was inseparable from Windows, a position Active Desktop made literal.
  • 2007: Windows Vista introduces SideShow. Asus ships the W5Fe with a 2.8-inch color display on the lid. Reviews praise the concept but note a lack of apps and rough edges. By 2013, SideShow is removed in Windows 8.1.
  • 2012: Surface RT and Windows RT launch. The OS looks like Windows 8 but can only run Store apps and the bundled Office. In July 2013, Microsoft takes a $900 million charge for unsold Surface RT stock, effectively admitting the product was misunderstood.
  • 2019: Windows 10X unveiled alongside the Surface Neo. Positioned for dual-screen, post-PC devices. By early 2020, the pandemic shifts demand to traditional laptops. Microsoft pivots 10X to single screens, then cancels it in May 2021.
  • 2021: Windows 11 releases with a design language heavily influenced by 10X. Windows on ARM matures, with x64 emulation arriving in Windows 11, learning from RT’s catastrophic lack of compatibility.

What to Do Now: Practical Takeaways

These historical detours aren’t just trivia—they give you a playbook for using Windows 11 more wisely today.

  1. Before buying an ARM PC, audit your software. Check if your must-have apps have native ARM versions or run reliably under emulation. Don’t assume. Microsoft’s compatibility lists are a starting point, but real-world testing matters.
  2. Tame your Widgets. If the Widgets board feels like Active Desktop’s noisy ghost, open Widgets, click the gear icon, and turn off the feeds you don’t want. You can keep weather and calendar without the clickbait.
  3. Adjust the taskbar to your taste. Windows 11’s centered layout might look modern, but if you prefer left alignment for muscle memory, it’s a simple flip in Settings.
  4. Turn off suggestions. In Settings → Personalization → Start, disable “Show suggestions occasionally in Start.” In Settings → Personalization → Lock screen, switch to “Picture” instead of “Windows spotlight” if you find the ads intrusive. In Settings → System → Notifications, uncheck “Offer suggestions on how I can set up my device.” These toggles are the modern answer to Bob’s overbearing friendliness.
  5. Be wary of UI experiments that feel stripped down. When Microsoft introduces a new simplified interface—like the recent mini Start menu in some Insider builds—remember 10X’s fate. Beta-test features but don’t assume they’ll land as-is, and have a backup if a clean install becomes necessary.

What to Watch Next

Microsoft’s lab isn’t closed. The next experiments are already visible in Windows Insider builds: AI Copilot integrated into the desktop, a potential overhaul of the system tray, and deeper cloud-hybrid features. The five failures above tell us the company will keep pushing envelopes. The question is always: Will this one be another RT—a painful lesson that costs users time and money—or another 10X, whose best ideas get folded smoothly into the Windows we rely on?

For users, the best defense is staying informed. When a new feature arrives, ask yourself: What older Windows component is this based on? If it’s a new interaction model (like voice commands or AI suggestions), decide early whether it helps your workflow or gets in the way. Microsoft’s history proves that the feature itself is rarely the final word—its second or third iteration is usually the one that sticks.