Microsoft's biggest wins, fails, and WTF moments of 2016

2016 was the year that Microsoft was expected to deliver on its promises. Instead, it exposed some holes in its once-ubiquitous ecosystem.

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2016: A year to remember... maybe?

2016 was a busy year for Microsoft wins and fails. From Windows phones to the Surface Studio, and Windows 10 to Minecraft, the company and its products dominated headlines in both hardware and software.

It was even occasionally pulled into the politics of the election year: Remember how alt-right trolls trained the sunny Tay chatbot to be a hater? And how chief executive Satya Nadella and others were summoned before president-elect Donald Trump?

Fortunately, most of Microsoft’s hits and misses were just about the technology. Let’s get started with the good, bad, and ugly of Windows 10.

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WTF: Windows 10's upgrade nightmare

Microsoft wanted to encourage users to take advantage of its free upgrade offer to Windows 10 before it expired at the end of July. But repeated nagware"Recommended" updates, and the ohmygod you DIDN'T practice of kicking off an upgrade after a user tried to close the dialog box was just an inexcusable violation of its customers' good faith and integrity. 

Without a doubt, this was the absolute worst misstep Microsoft made during 2016, poisoning the minds of those on the fence and leading to numerous "What were they thinking?! facepalms from those who saw the company in a more positive light. There was even a lawsuit.

All in all, it left Microsoft looking like less like a model for working with customers and more like a crazy ex drunk-texting you to try and get back together.

action center Windows 10 anniversary update expanded
Mark Hachman

WIN: Windows 10 Anniversary Update

Upgrade outrage aside, Windows 10’s Anniversary Update brought with it a slew of new features, including a move to pen-based computing, Windows Ink.

It wasn’t perfect—recall how the update broke Webcams and caused some PCs to freeze. On balance, however, the Windows 10 AU’s improvements to the features you use most justified its inclusion as one of Microsoft’s victories of 2016. Expect to see more soon: Next up is the Creators Update, due sometime in spring 2017. 

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FAIL: Windows Ink

Windows Ink's electronic-inking capabilities are a solid concept, and we anticipated seeing them come to fruition as part of Microsoft's Anniversary Update. Unfortunately, Microsoft hasn't quite delivered the goods.

In October, Microsoft tried again. We looked at two new features for Windows Ink: the ability to interpret inked equations, and a cool new Replay feature for playing back inked illustrations. Neither impressed. The story here, though, is Ink's potential, not its reality. We're looking forward to 2017 to see if Microsoft can change our minds. 

An Ubuntu Bash shell window on Windows 10

WIN: Bash on Windows

The inclusion of Linux within Windows 10 was wholly unexpected in a number of ways, not the least of which was Windows' history of dismissing the open-source OS. But there it is, embedded in Windows 10's Anniversary Update. Whoa!

Linux never achieved any sort of truly competitive status, but if you're a fan, it's a great bonus feature of Windows. Hell froze over, indeed.

patriots surface Microsoft

FAIL: Surfacegate, or Microsoft versus the New England Patriots

Poor Microsoft. First the lamestream media couldn't help but call its Surface tablets "iPads." We were treated to Surfaces being rammed into Johnny "Football" Manziel's head or thrown down in disgust by Aaron Rodgers. A starring moment at the Super Bowl was a rare bright spot.  

The New England Patriots displayed a particular animosity toward the Surface, blaming Microsoft for tablet failure at critical junctures. Then head coach Bill Belichick emphatically benched the Surface tablets in October.

Microsoft may not have felt any long-term impact from Surfacegate, but it wasn't especially helpful in mainstreaming the technology, either.

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WIN: Qualcomm partnership puts Windows 10 on low-end PCs

A better future for Windows tablets could be just around the corner, though. Windows RT tried and failed to create a new class of Windows 10 PCs, but Microsoft's trying again, partnering with Qualcomm to put Windows 10 on low-end PCs. This time around, Microsoft is adding Windows 10 and its legacy of traditional Win32 apps on the ARM hardware.

Note, however, that Microsoft is using an emulator to enable Win32 compatibility, and emulators can be notoriously slow. If Microsoft and Qualcomm deliver "good-enough" low-cost computing, that could be a nice shot in the arm for a struggling PC market. Finally, Windows RT done right!

minecraft windows Microsoft
Patrick Moorhead

WIN: Minecraft Education Edition

Microsoft bought Mojang and its hit game, Minecraft, for over $2 billion in 2014—and the Internet collectively gasped in shock. Two years later, though, and Microsoft has carefully shepherded Minecraft into becoming a bona fide gaming treasure. 

According to Microsoft chief executive Satya Nadella, Microsoft bought Mojang to encourage science education. In January, Microsoft announced Minecraft: Education Edition, keeping that vision alive. Cynics may call this a way to keep students on Windows and off Chromebooks, Microsoft's primary competition in the schools. Nope. Keep it up, Minecraft team—you're getting it right.

Mikael Ricknas


Windows phones still have have some small life in them, but the Lumia line that Microsoft bought for $7.2 billion in 2013 is basically no more. Microsoft signalled as much in January, and throughout the year small signs pointed to the Lumia’s demise: shuttering social media accounts, running out of stock in the UK's Microsoft Store, and handing off Windows phones to hardware partners like HP and Acer. 

Let’s just take a moment to remember the Lumia 1020, the pride of Windows phones, shall we? A 41MP camera—it’s doubtful we’ll ever see its like again. Speaking of which...

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Mark Hachman

FAIL: Windows 10 Mobile's future

After shrinking to well under one-percent market share, Microsoft’s mobile OS is on life support. Surprisingly, that didn't stop Acer’s Liquid Jade Primo, Alcatel’s Idol 4S, and the HP Elite x3 from their debuts as third-party Windows phones—and to be honest, some were suprisingly good. 

But when Windows faithful on Windows blogs are giving up on Windows phones, the OS is done. Sure, there may be a Surface phone out there, but it’s the mythical beast of mobile devices. 

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WIN: Skype Translator goes live for all

Finally, our Star Trek future is here. 

In January, Microsoft’s Skype finally pushed Skype Translator to all Windows users. Skype Translator currently offers voice-to-voice translation for seven languages including English, French, German, Italian, Mandarin, Portuguese, and Spanish. Dozens more are available via text chat, and it now even works with mobile phones!

Ignore for a moment that Skype (Win32), Skype Preview (Windows 10) and Skype for Business (Office 365) are still different apps, with different capabilities—and Skype Translator only works on the Win32 app for now. (Skype corporate vice president Amritansh Raghav tells me this will begin to change in 2017.) Skype Translator is amazing technology, and it’s free.

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FAIL: Where did HoloLens go?

Sorry, Microsoft: After touting HoloLens as the future of augmented reality in 2015, Microsoft’s HoloLens basically vanished during 2016—forcing us to sneak into a hotel room to test it.

HoloLens seems to be just over the horizon. It will be intimately tied to the Windows 10 Creators Update due this spring. You can play with it at Microsoft Stores. Paint 3D Preview is an app specifically designed for HoloLens. Anyone wanna send Actiongrams

The fact remains, however, that it’s been about two years since Microsoft first demonstrated the product, and attention spans wane. Windows Holographic may power a number of low-cost head-mounted displays from partners like Acer and Asus, but Microsoft’s augmented-reality future still costs thousands of dollars, and that’s just for developers. Remember, too, that HoloLens uses Intel’s Atom chip—you know, the one Intel cancelled?

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Mark Hachman

WIN: Microsoft Surface Hub

Microsoft's Surface Hub offers up to 84 inches of droolworthy 4K goodness, a perfect solution to your conference-room Skype issues, and a digital whiteboard to boot. After a couple of delays, Microsoft began shipping the Surface Hub in March, and there seems to be solid availability from its resellers. Microsoft says the Hub is going gangbusters, relatively speaking. (I'm still wondering why CDW is selling the $22,000 version for over $30K at press time, without warranty, though.) 

Check out our hands-on with the Surface Hub for more of our thoughts. Sure, this is a productivity machine through and through, but we still want one for our living rooms. Make it happen, Microsoft.


FAIL: Where are all the Android/iOS/Win32 apps again?

In 2015, Microsoft's Build developer conference was filled with promise: Microsoft announced "bridges" that would help port Android and iOS software to the Microsoft UWP platform. In 2016, Project Centennial, a similar bridge between Win32 apps and Windows, was announced.

But then, in November, 2015, Microsoft killed Project Astoria, its Android-to-Windows bridge. Islandwood, the iOS bridge, is at version 0.2. Centennial finally began pushing Win32 apps to the store in September, but with little more than Evernote.

Microsoft's answer now seems to be Xamarin, a company Microsoft bought that promises all of the capabilities of Astoria, Islandwood, Centennial, and more in one tool.  The name on the door doesn't matter, though. The question remains: Where are all the apps?

forza horizon 3

WIN: Microsoft Xbox Play Anywhere

As a cheapskate gamer, I'm happy picking up two- or three-year-old AAA games and playing them on my Xbox One. But PC gamers with $4,000 tricked-out rigs tend to look down on we downmarket console gamers.

In 2016, Microsoft's Xbox Play Anywhere satisfied both camps. Buy one of its franchose games from the Microsoft Store (such as Forza Horizon 3, seen here) and Microsoft bundles copies both for the Xbox and the PC, allowing you to pick up where you left off on either platform. 

microsoft edge

FAIL: Microsoft's slow slide in browser share

Remember how terrified the market was of Internet Explorer’s integration into Windows? Those days seem so long ago, as Microsoft’s browser market share continues to slide. 

In May, NetApplications said Google’s Chrome market share had passed that of Internet Explorer. That same month saw Firefox’s total share climb above that of Edge and Internet Explorer, worldwide, according to StatCounter. In any event, there’s been a clear downward trend as users (finally) shift away from Internet Explorer at Microsoft's behest—and use Edge to download Chrome or another browser. 

We think Edge was one of the most improved features  of the Anniversary Update—but not enough users agree. Microsoft had its shot to establish Edge, and it missed.

Head to head with the Xbox One and Xbox One S

WIN: Microsoft's Xbox One S and Project Scorpio

Scorpio, due by holiday 2017, promises six teraflops of computing power—more than double that of the existing Xbox One. And though we’re a little skeptical of Microsoft’s claims of 4K gaming, we’re at least hoping for games that scale up to 4K resolution. Fasten your seat belts: 2017’s going to be a bumpy ride in the gaming space!

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FAIL: Microsoft Band

Microsoft’s 2016 hardware garbage fire continued with the demise of the Microsoft Band, its first wearable. When Microsoft launched the Band 2, we were told that the next step—the magic third iteration of Microsoft’s “Rule of Three”—would be to embed Windows 10 within it. That apparently never happened, and it’s safe to say that the Band is likely dead.

Microsoft can take some comfort in the fact that Fitbit bought Pebble, Intel cancelled its Basis Peak smartwatch, and the wearables market has become increasingly fragmented. Even Apple has begun touting the fitness capabilities of the Apple Watch—proving I was wrong about customers' desire for a smartwatch

Microsoft’s Band 2 exited as the best fitness band on the market, but with limited battery life and no waterproofing, it had no hope of survival.

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Mark Hachman

WIN: Microsoft's Surface Studio

We doubt many of you will be paying over $4,000 for an digital artist’s easel like the Surface Studio. But we know you'll be tempted. Just look at it! Big, beautiful—and that reclining display surely has the Mac crowd going gaga. There's even a clever little accessory to go along with it: the Surface Dial.

Honestly, the Surface Studio was such a hit that it even overshadowed the revamped Surface Book with the upgraded Performance Base. That's pretty darn good.

Of course, with that lofty pricing, it's unlikely the Surface will run up the sales numbers of, say, a Surface Pro 4. But the Studio is definitely drool-worthy, earning it a clear victory for Microsoft. Bravo, Microsoft! Encore!

tay ai Microsoft tay

WTF: Microsoft's chatbot becomes a tool of the alt-right

In March, when Microsoft’s chatbot debuted, the Internet was different. For a few hours, maybe a day, Tay’s forced Millennial edginess made her the butt of jokes, and that was okay. 

The tone changed rather quickly when white supremacists taught Tay to repeat anything they said. In retrospect, Microsoft’s was as good a metaphor for 2016’s Internet as you’re likely to find: an innocent device corrupted by the alt-right, transformed into a tool for misogyny and hatred. Microsoft promised to bring Tay back when Microsoft could fix her “vulnerability,” but that hasn’t happened. Instead, Microsoft tried again with a chatbot named Zo, smartly keeping politics out of the discussion.

To sum up: we’d say that 2016 was the year that the market judged Microsoft’s 2015 promise of a ubiquitous Windows ecosysem—and judged it rather harshly, in places. But we’re still seeing strong signals from Redmond that it plans to lead in both consumer gaming and in its Surface tablets during 2017, with services sealing up any gaps left in the device landscape.

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