Microsoft’s Most Embarrassing Product Failures

Microsoft’s Most Embarrassing Product Failures
A new Zune portable digital music player. (Photo: Scott Olson, Getty Images)

Microsoft is responsible for bringing many of us into the digital realm, introducing generations of consumers to the PC. Even today, the Windows operating system is used by more than a billion people worldwide. Beyond Windows, Microsoft and its brand Xbox have been a driving force behind the growth of gaming, Office is the most widely used productivity suite in the world, and Internet Explorer was, at one point, the gateway to the internet for 95% of online users.

Microsoft’s influence on our lives can’t be overstated. And yet, this hugely successful and resource-rich company has had its fair share of failures over the years. The same company that dominates desktop OS market share and sells millions of Surface devices each year has a checkered past filled with embarrassing product releases, devastating missteps, and confusing marketing.

Let’s head into our time machines and look back at Microsoft’s worst failures.

Want more schadenfreude? Check out Google’s most embarrassing failures.

Microsoft Band

Microsoft Band 2 (Photo: Chris Mills/Gizmodo)Microsoft Band 2 (Photo: Chris Mills/Gizmodo)

I really thought this wearable had potential. But when Microsoft released the second edition without addressing the major complaints of the first, it set the fitness tracker on a path to extinction. It’s a shame, because the Band was packed with fitness features and smartwatch functionality, and was uniquely compatible across Android, iOS, and Windows phones.

What’s so frustrating is that the Band’s major downfall — poor comfort — seemed easily fixable. And yet, when Microsoft released the Band 2, it was only slightly more tolerable to wear. Then there was the issue of reliability. Not with the platform — the Band was one of the most accurate fitness trackers available at the time — but with the rubber material, which was prone to cracking.

Microsoft quietly switched to a thicker, more durable band, but it never added waterproofing or improved the battery life beyond two days. The fitness tracker also wasn’t cheap, and at a time when non-Apple Watch wearables were struggling to make any noise, the industry needed a more refined product. After two short years, the Band was discontinued in 2016.


Microsoft Bob (Screenshot: LGR/YouTube, Other)Microsoft Bob (Screenshot: LGR/YouTube, Other)

Remember Clippy? Before the friendly paperclip, there was Bob, a big yellow smiley face assistant, and his dog Rover. Bob was a software product with a gamified user interface meant to help novice computer users navigate Windows. Along the way, various anthropomorphic “assistants” would guide you through rooms housing everyday objects that correlated with software. For example, a pen and paper represented the word processors, or a clock was a calendar.

This sort of thing was useful at a time when some people had no experience using computers. However, Bob was harshly criticised for its lack of imagination, annoying characters, and overly complex interface. It sold poorly and was discontinued one year after launch. At least it inspired Clippy (real name: Clippit), right?

We’ll see if the promised Metaverse is any different.

Windows Me

Windows Me (Screenshot: LGR/YouTube, Other)Windows Me (Screenshot: LGR/YouTube, Other)

Not even a cute name could save Microsoft Me from being dubbed the worst Windows ever. Released in 2000 as the third update to Windows 98, Microsoft Millennium Edition (or Microsoft Me), was meant as a stopgap between Windows 98 and XP, which was in development at the time Me arrived and would be released to the public a year later.

Initially, reviews for Windows Me were mixed, with several sites praising the OS for its improved hardware and software compatibility over even Windows 2000 (which had also been released as a business-oriented OS seven months earlier). Others, like PCWorld’s Dan Tynan (who dubbed it the “Mistake Edition”) criticised its poor reliability. After all, Windows Me was clinging on to an ageing 9x platform and Windows 2000 wasn’t ready for consumers.

In the end, Windows Me was only ever a bridge between the old and the new Windows, and not enough people felt compelled to spend money on an OS that would only stick around for a year. Although it was a failure, Windows Me improved boot speeds and introduced several innovative features still used today, including system file protection, auto-update, hibernate, Movie Maker, photo sharing, system restore, and more.


Zune HD (Photo: Dan Nosowitz/Gizmodo)Zune HD (Photo: Dan Nosowitz/Gizmodo)

Beloved by those who owned one, the Zune ultimately couldn’t keep up with the iPod (RIP). It was a matter of too little, too late. The iPod was already taking off when Microsoft released its competitor, but nothing was going to stop Apple — not even Zune’s, erm, squirting feature.

When it arrived, the Zune was little more than a Microsoft-branded iPod. It was a perfectly capable music player but failed to address the problems people had with Apple’s device. That’s not to say it didn’t have its own unique features; the Zune came with a Wi-Fi chip before the iPod, one that allowed other Zune-sters to share songs and photos (with limitations). Microsoft also beat everyone to the punch with Zune Pass, a $US15 ($21)/month all-you-can-listen subscription service (with 10 free song downloads a month!). The Zune HD was also among the first devices with an OLED display — how cool!

Anyway, the Zune was bulkier than the iPod, it didn’t have the same apps and accessories ecosystem, and its video codec support was restricted. The Zune’s limited success can also be largely blamed on marketing blunders — Microsoft just couldn’t grab the ears of customers already making their way to Apple stores.

Groove Music

Groove would redirect to Spotify (Image: Microsoft)Groove would redirect to Spotify (Image: Microsoft)

Zune Music Pass would be rebranded in 2012 to Xbox Music, an attempt from Microsoft to make Xbox its multimedia platform. It didn’t catch on, so before releasing Windows 10, the company rebranded the service once more to Groove. By the time Groove arrived, Microsoft’s music streaming efforts had already failed. Within a few years, the company discontinued the streaming service, redirecting users to Spotify. It then shuttered the Groove Music apps on iOS and Android.

Groove music lived on for a while longer as a media player before being replaced this year by a new Windows 11 “Media Player” app, a successor to the legacy Windows Media layer.

Microsoft Kin

Microsoft Kin (Photo: Matt buchanan/Gizmodo)Microsoft Kin (Photo: Matt buchanan/Gizmodo)

Remember the Microsoft Kin? I don’t, either. This short-lived mobile phone was purpose-built for social networking. There were two models, the Kin One and the Kin Two. The One was egg-shaped like a Tamogachi and the front slid up to reveal a keyboard below, while the Two was more similar in shape to a Motorola Droid or Danger Hiptop (or T-Mobile Sidekick). I mention the latter because Microsoft purchased Danger for $US500 ($694) million in 2008 and the Kin was a spiritual successor to the Hiptop.

Where the Hiptop, or Sidekick, thrived from 2002 to 2010, the Kin was abandoned after just two months. Verizon sent all unsold units back to Microsoft, pulling online sales entirely. Why didn’t it catch on? Some point to development hell, with Engadget reporting that Microsoft’s decision to use Windows CE instead of sticking with the Sidekick platform (which, again, it acquired for a huge sum) set back the project by 18 months.

It didn’t help that the phones had tiny screens, were lacking important apps (and couldn’t download third-party apps), and were running on a fluttered, unintuitive OS. Reports put the Kin’s total sales figures in the hundreds on the low end to “south of 10,000” on the high end. Either way, it was nowhere near successful enough to compete against Apple.

Windows Phone (and Lumia)

Microsoft Lumia 950 (Photo: Mario Aguilar/Gizmodo)Microsoft Lumia 950 (Photo: Mario Aguilar/Gizmodo)

Ctrl+c, Ctrl+v. Windows buys a smartphone giant, takes over operations, then shutters its efforts within a few years. Sound familiar? Sadly, this time it happened to our beloved Nordic friends at Nokia.

Microsoft’s answer to iOS and Android, Windows Phone was a simple, easy-to-use smartphone OS that was much more responsive than any Android phone at the time. Launched in 2010 as a successor to Windows Mobile, Windows Phone differentiated itself with its “Metro” interface, which consisted of colourful “live tiles” that updated regularly to display relevant information. Samsung, HTC, Dell, and LG took the plunge, releasing handsets powered by Microsoft’s OS. At one point, Windows Phone was supported by some of the best hardware available, including the Nokia Lumia 808 Pureview with its 41MP camera.

The problem was simple: Windows Phone lacked apps. Microsoft couldn’t get developers to port their apps over to the OS. As such, owning a Windows Phone meant missing out on the growth of mega-popular apps like Instagram and YouTube. Hoping to revive interest in the platform, Microsoft outright purchased Nokia and eventually released devices under the “Microsoft Lumia” brand. It was too late. Windows Phone was faltering, its companion Windows 8 desktop OS was a disaster, and the apps weren’t coming fast enough. Windows Phone reached its end of life on January 14, 2020.

Windows Vista

Put your hand up if you’ve been waiting for this one. Was Windows Vista really that bad? In some ways, yes. In others, no. After a disastrous development cycle, Windows Vista, the follow-up to Windows XP, was released to the public in 2017. Despite its currently tainted reputation, Vista brought some good ideas to the table, some of which were adopted in the latest Windows 11 OS. The problem was that some of the features, like the transparent (sound familiar?) Aero interface, were too advanced for the majority of PCs on the market.

Microsoft was eventually hit with a lawsuit alleging the company misled customers by putting a “Vista capable” sticker on computers when they could only run Vista Home Basic, the entry-level version of the operating system. That was just the tip of the iceberg. Because of its complexities, Vista was even slower than Windows 95 when it launched, and since it required new drivers, many graphics cards and peripherals didn’t work properly. In the end, the adoption rate was low and Microsoft kept Windows 95 around for longer than scheduled. Vista, for every modern feature it introduced that we now take for granted, goes down in history as one of Microsoft’s biggest failures.

Windows 8 and Windows RT

Windows 8 (Image: Microsoft)Windows 8 (Image: Microsoft)

With the PC market facing pressure from smartphones and tablets, Microsoft took a massive risk by releasing an OS that didn’t look, feel, or operate like any Windows version before it. This was at a time when the popular and largely beloved Windows 7 was only three years old.

When distilled down, Windows 8 was an operating system built for touch — an environment that bridged desktop with mobile so it could be used on a tablet as readily as a massive gaming rig. Unfortunately, people just didn’t respond to all of the changes. The colourful Tile-based interface stripped from the Zune and Xbox was confusing and unfamiliar, the missing Start button left people scratching their heads, and the Windows Store was empty save for some sketchy apps.

If there was one problem Microsoft needed to solve above anything else, it was the disconnect between the touchscreen interface and the traditional desktop mode. These felt like distinct operating systems, one optimised for tablets and touchscreen laptops and the other for non-touch devices. If you didn’t have a touchscreen, the tile interface was a hassle to navigate; likewise, those without a mouse and keyboard couldn’t take advantage of the desktop interface. Microsoft solved that issue with Windows 8.1, giving users the ability to boot directly to the desktop. But the damage was already done, and Windows 8 would be quickly replaced by the warm, familiar arms of Windows 10.

Windows RT, a spinoff of Windows 8, was another confusing failure. Designed as a lightweight version of Windows 8 for tablets running on ARM, Windows RT was severely limited due to its reliance on a struggling app store. Eventually, third-party tablet makers skipped Windows RT altogether and opted to put the full Windows 8 on their devices.


Harman Kardon Invoke powered by Cortana (Screenshot: Harmon/Kardon)Harman Kardon Invoke powered by Cortana (Screenshot: Harmon/Kardon)

Microsoft’s virtual assistant exists today, but not in the role it was born to play. Again, Microsoft was late to the party here, launching Cortana long after Google Assistant, Amazon’s Alex, and Apple’s Siri had eaten up market share. Named after an AI in the video game Halo, Cortana launched on the ill-fated Windows Phone before being integrated into PCs in 2015. On paper, Cortana looked like a success due to the millions of users who had access to it by simply owning a Windows PC. In practice, nobody was talking to the assistant.

Cortana didn’t stand a chance once Windows Phone failed. Being integrated into laptops and desktops just isn’t as useful as being the go-to assistant on a mobile device. Microsoft tried to expand Cortana’s reach with the Harmon Kardon Invoke speaker powered by Cortana (and the Johnson Controls GLAS Thermostat), but it otherwise failed to get enough third-party support. Microsoft eventually removed Cortana from Windows Search and disabled it by default in Windows 11.

Xbox “The Duke” controller

Original Xbox Duke controller on the right (Screenshot: TheRelaxingEnd/YouTube, Other)Original Xbox Duke controller on the right (Screenshot: TheRelaxingEnd/YouTube, Other)

I was tempted to add the Xbox One to this list due to Microsoft’s terrible decision-making in the buildup to its release. Then I remembered The Duke. There is no denying the outrage Microsoft faced when it revealed the first-generation Xbox controller, nicknamed The Duke.

Why the Duke? It was huge, ugly, and just awkward. When Microsoft introduced the original Xbox controller, fans reportedly threw garbage at Seamus Blackley, the console’s designer. Xbox didn’t want to build such a giant controller, but its hands were tied when the circuit boards were larger than anticipated. The Xbox controller ended up being nearly three times larger than the PlayStation’s DualShock controller.

A few months after the Xbox launched with the Duke controller, the Japanese version arrived with a sleeker Controller S. It didn’t take long for Microsoft to make the Japanese version the default controller for Xbox worldwide. And yet, the Duke would go on to live another life thanks to Hyperkin, which released a Duke-inspired controller for Xbox One and PC in 2018 (which is still available as of writing).

Internet Explorer

Internet Explorer (Photo: monticello, Shutterstock)Internet Explorer (Photo: monticello, Shutterstock)

IE was a massive success until it wasn’t. Launched in 1995 as an add-on package before becoming a part of the Windows 95 operating system, Internet Explorer quickly rose to fame, defeating Netscape in the browser wars before reaching a peak market share of around 95% in 2003. For people who grew up in the ‘90s and early 2000s, IE was the gateway to the internet — an open door to a vast digital world.

The demise of this once king of browsers was just as swift. Microsoft stubbornly left the browser out to dry while competitors like Mozilla arrived with more features, faster loading speeds, and support for international web standards. When Google’s Chrome browser entered the market, IE’s fate was decided.

Chrome was faster, cleaner, and presented sites as they were meant to be. After a rapid decline, IE would go from a market share of 65% as recently as 2009 to less than 1% today. It would eventually be replaced by “legacy Edge,” which would be replaced by “new Edge,” Microsoft’s current Chromium-based browser. On June 15, 2022, Microsoft dropped support for Internet Explorer, ending an era that lasted for 26 years.