[caption id="attachment_15596" align="aligncenter" width="618"] Healthcare.gov didn't exactly experience a smooth start.[/caption] This year had its winners in the technology world, true, but there were also some spectacular losers:

BlackBerry 10

Did BlackBerry executives really think that BlackBerry 10 would spark a miraculous turnaround, or were they simply going through the motions of promoting it? That’s the key question for the history books. To be fair, BlackBerry 10 was a thoroughly modern operating system, with a polished interface and several intriguing features. But with its market-share slipping, BlackBerry was never going to prosper with a modern OS—it needed something so spectacularly next-generation it would make even the most diehard Apple fan drop his or her iPhone 5S and sprint for the nearest smartphone emporium. It’s no surprise, then, that the massive bet on BlackBerry 10 turned into a massive whiff: not only did the company only sell 1.9 million smartphones last quarter—in contrast to 3.7 million units the quarter before—but most of those devices ran BlackBerry 7, which BlackBerry 10 was supposed to replace. Whoops. BlackBerry is rapidly remaking itself as an enterprise-services firm as we speak, but it’s an open question whether it can pull off this latest transformation.

Microsoft’s “Devices” Strategy

On paper, Microsoft’s decision to start manufacturing hardware in-house made perfect sense: by controlling the entire technology stack, the company could assure a certain degree of quality (hey, it worked for Apple). In reality, however, that decision resulted in messiness: first, its inaugural device—the Surface tablet-PC-hybrid-thingie—failed to sell. Second, OEMs that had stood by Microsoft for years—including Hewlett-Packard—began to view their partner in Redmond as more of a competitor, which could eventually result in still more Chromebooks and Android devices hitting the market. Rather than pull back on its strategy, Microsoft decided to double down with the Surface 2, and it remains to be seen whether that device will sell any better than the first one. As for alienating the OEMs—well, it’s probably no coincidence that Chromebook adoption picked up this year. Yeah, to say Microsoft’s newfound focus on devices wasn’t an outright success is putting it mildly.

Snapchat

Snapchat is an app that allows people to send messages that vaporize within a few seconds of being opened. That’s attracted millions of users, and Snapchat’s executives reportedly fielded a $3 billion buyout offer from Facebook earlier this year (rumors also suggest that Google may have floated a higher bid). Those executives turned it down; Snapchat CEO Evan Spiegel has reportedly tabled any discussion of an acquisition, or even a major round of venture funding, until early 2014. That decision (some might call it hubris) could come back to bite them later. Other companies offer messaging apps that mirror Snapchat’s functionality; moreover, Snapchat’s audience is reportedly composed mainly of teenagers and younger twentysomethings, which is a demographic known for quickly abandoning platforms in favor of some new, shinier thing. If Snapchat pulls a Groupon and collapses within the next few years (or months), Spiegel will probably regret not taking that reported buyout when he had the chance.

Healthcare.gov

Originally launched with high hopes, the government’s online portal for the Affordable Care Act (ACA) quickly transformed into a tech disaster for the ages: amidst repeated crashes and glitches, customers found themselves unable to sign up for new accounts or enroll in health insurance. The contractors tasked with building the site immediately began pointing fingers at each other; executive-branch officials trekked up to Capitol Hill to take their public tongue-lashings. In a panic, government officials promised a “surge” of tech workers to fix the underlying infrastructure. “The website is getting better each week, as we work to improve its performance, its stability, and its functionality,” U.S. chief technology officer Todd Park said in Nov. 13 testimony before the House Oversight Committee, according to The Verge. “We have much work still to do, but are making progress at a growing rate.” While the site’s working better as 2013 reaches its close, it’s clear that the debacle’s aftereffects will echo for a long time to come.

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Does anyone still use Facebook’s misbegotten attempt at “skinning” the Android OS? Besides Facebook employees, we mean?   Image: healthcare.gov