“Now, this is real simple,” President Obama told a crowd at Prince George’s Community College, in Maryland, in late September. “It’s a Website where you can compare and purchase affordable health-insurance plans, side by side, the same way you shop for a plane ticket on Kayak … same way you shop for a TV on Amazon. You just go on, and you start looking, and here are all the options.”

As we all now know, the bug-infested Website healthcare.gov turned out to be anything but “real simple.” After the site’s disastrous October 1 launch, the administration organized a frantic rescue effort shepherded by Jeffrey Zients, who is to become Obama’s chief economic adviser in January, and on December 17, the administration tapped Microsoft executive Kurt DelBene to lead the effort to build out the rest of the Website. The site is working better (but as of this writing still not perfectly) for consumers, though the complications it has unleashed for President Obama will be even harder to fix. The New York Times called the broken Website a “crisis that suddenly threatened his presidency,” and according to a CBS News poll, Obama’s job-approval rating has plunged to an all-time low. Americans’ approval of the Affordable Care Act has also dropped to its lowest level since CBS News began polling support for the law.

The story of how the Obama administration and the Centers for Medicare and Medicaid Services (CMS), the agencies tasked with implementing the Affordable Care Act got it so wrong is still unfolding. Much of the blame has to fall on an insular White House that didn’t want to hear about problems, and another chunk has to land on CMS, which instead of hiring a systems integrator, whose job it would have been to ensure that all the processes feeding into healthcare.gov worked together, kept that role for itself. As anyone who has worked with the federal government on such projects knows, it is utterly inept when it comes to technology. “The government continues to struggle with how best to acquire the expertise to integrate technology,” says Stan Soloway, the C.E.O. of the Professional Services Council, which represents contractors who work with the government. Soloway has a scary stat, which is that of the 80,000 information-technology workers in the federal government, for every one person under 30, there are 10 people over 50.

That lack of expertise explains why in building healthcare.gov, the government turned to industry contractors; in particular, to CGI Federal, a subsidiary of CGI Group, a Canadian company. To those uninitiated in the dark art of government contracting, it seems scandalous that CGI, a company most Americans had never heard of, a company that is not located in Silicon Valley (where President Obama has plenty of Internet superstar friends who could have formed a dazzling brain trust to implement his signature legislation) but rather in Montreal, could be chosen as the lead contractor for the administration’s most important initiative. While right-wing news outlets have focused on the possible relationship between Toni Townes-Whitley, senior vice president for civilian-agency programs at CGI Federal, and Michelle Obama, both of whom were 1985 Princeton graduates, CGI’s selection is probably more an example of a dysfunctional system than it is a scandal. “A lot of the companies in Silicon Valley don’t do business with the government at that level [the level required for federal contracting],” explains Soloway. “It is very burdensome, and the rules make it very unattractive.” Indeed, government contractors have to meet a whole host of requirements contained in a foot-thick book, including cost accounting and excessive auditing, to prove that they are not profiting too much off the American taxpayer. Hence, there tends to be a relatively small, specialized group of companies that compete for this work, even on such critical matters as healthcare.gov.