In 2008, the image of a presidential hopeful glued to his BlackBerry was something novel in American politics. Today, in a world of iPhones and smartwatches, it looks out of date.

In his two terms as president, Barack Obama has led the nation during the mass consumer adoption of the internet. His victories at the ballot have largely been credited to an army of nerds who drove his tech-savvy campaigns with talent from Twitter, Facebook, and Google. It was Harper Reed and "Narwhal" that took down Mitt Romney and "Orca" — not merely a campaign ad that was more clever than the other guy’s.

Today, Obama’s cunning campaign looks like an anomaly in the face of two gargantuan failures: Healthcare.gov and the monstrosity of NSA spying. When the nerds marched in to build Healthcare.gov, they didn’t come from Google or Facebook; they came from Canadian firm CGI Federal and dozens of other insider contractors. When the nerds of the NSA marched under legacy orders from President Bush, Obama renewed their mission and even expanded their intrusive, unprecedented surveillance of American citizens and efforts to crack the security measures that ensure privacy for everyone on the internet. These aren’t superficial matters; once we begin to start administering our laws electronically, the systems of administration will effectively enforce the limits of our freedom. With the internet now a staple in the lives of millions of citizens, our government can’t remain behind the curve.

The president, of course, is just one man. Not all of the technological failures can be attributed to Obama, and they probably shouldn’t be; perception of the president’s power has arguably exceeded the office’s authority by a vast margin as the scope of the executive branch has expanded over the past century. Healthcare.gov — the massive system which was supposed to be a primary expression of Obama’s landmark Affordable Care Act — was mired by a nightmarish federal IT procurement system that the president inherited along with years of Republican efforts to derail implementation of the ACA. And the intelligence community’s unprecedented, expansive spying programs were already snowballing from the days of 9/11 and the Patriot Act. But that won’t keep the public, or Obama’s opponents, from holding the deep technology problems of his second term over his head for the remainder of his presidency and beyond. The president can’t blame all his failures on preexisting conditions.

The administration seems to think of technology the way consumers do — a commodity that can easily be bought. In November, Obama said he wouldn’t have launched Healthcare.gov if he had known it wasn’t going to work, but that’s ultimately a poor excuse; Obama was responsible for the incoherent management mess that didn’t understand how to develop a website or to see the red flags along the way. In the years following passage of the ACA, no single person was responsible for Healthcare.gov’s development. Instead, responsibilities for managing the project and its 55 contractors were spread across several agencies and deputies who weren’t focused on the site’s development full-time. Imagine a handful of Google engineers trying to build Android from the ground up in their spare time.

The president’s decision to delay certain crucial policy measures for political reasons also impacted the process, leaving the engineers without the specifications they needed to build a fully functional site until the final hours. That kind of ragtag approach might work if you’re building a campaign website, but not when you’re building a massive health-care exchange that millions of Americans must rely upon.

To fix the site the president called for a "tech surge," drawing an unfortunate comparison to another surge that also didn’t turn out well for the US. The Healthcare.gov surge added workers at all levels, expanding an already bloated project. "‘Tech surge’ is just a couple buzzwords thrown together," a source familiar with CGI Federal told The Verge in an email. More than two months after launch and an estimated $600 million in development costs, the website still faces problems.

The companies Obama is now enlisting to help fix the health-care site — America’s technological brain trust — are starting to turn their backs on him. On Tuesday, at a White House meeting meant to get recommendations on Healthcare.gov from giants like Yahoo’s Marissa Mayer, Netflix’s Reed Hastings, and Google’s Eric Schmidt, executives reportedly steered the conversation towards government spying. Obama wanted to talk about the insurance site. "That is not going to happen," one executive reportedly said. "We are there to talk about the NSA." Yahoo, Google, Apple, Microsoft, Facebook, and others have filed lawsuits or supported briefs against NSA surveillance, and last week a coalition of major tech companies sent an open letter to the White House demanding reform.

It’s not clear how Obama ended up supporting the intelligence community’s massive, questionable programs. As a senator and presidential candidate, Obama encouraged prudence and caution when it came to laws like the Patriot Act, but as president, Obama has extended Bush’s legacy of spying. Obama may not have been able to predict that a single contractor would leak the nature of NSA spying to the world, but that he enabled them in secret is arguably more concerning.

As commander in chief, there’s little argument that the NSA’s programs are directly Obama’s responsibility. While the White House has denied knowledge of some of the agency’s programs, like spying on the personal phones of world leaders, the president has defended the most controversial programs which indiscriminately surveil American citizens. Obama’s initial defense of the NSA’s programs may bite him in the long run now that congressional opposition is mounting, and since a federal court has just found for the first time that the government’s dragnet phone surveillance program is likely unconstitutional.

Any president’s second term is effectively far shorter than four years; with midterm elections and the natural abatement of political power, presidents famously become "lame ducks," sometimes long before their tenure ends. According to some wonks, Obama’s second term could meaningfully be up as soon as next year. If he can’t deliver on Healthcare.gov or NSA reform by then, the president’s legacy could already be sealed.

If Obama’s technology legacy has a lesson, it’s that the government can’t waste any more time transitioning to the internet age. It must learn how to quickly and efficiently utilize technology to carry out the nation’s laws, and know enough not to willfully break it. It’s time for Obama to ditch his BlackBerry. We can’t afford another presidency that learns the hard way.