The Times has an in-depth investigation exploring why, and how the Obamacare exchange web sites messed up so royally. While there were ancillary causes to setback the project, including political gridlock, a lot of it seems to be based on poor project management:

Deadline after deadline was missed. The biggest contractor, CGI Federal, was awarded its $94 million contract in December 2011. But the government was so slow in issuing specifications that the firm did not start writing software code until this spring, according to people familiar with the process. As late as the last week of September, officials were still changing features of the Web site, HealthCare.gov, and debating whether consumers should be required to register and create password-protected accounts before they could shop for health plans.

One highly unusual decision, reached early in the project, proved critical: the Medicare and Medicaid agency assumed the role of project quarterback, responsible for making sure each separately designed database and piece of software worked with the others, instead of assigning that task to a lead contractor.

Some people intimately involved in the project seriously doubted that the agency had the in-house capability to handle such a mammoth technical task of software engineering while simultaneously supervising 55 contractors. An internal government progress report in September 2011 identified a lack of employees “to manage the multiple activities and contractors happening concurrently” as a “major risk” to the whole project.

While some branches of the military have large software engineering departments capable of acting as the so-called system integrator, often on medium-size weapons projects, the rest of the federal government typically does not, said Stan Soloway, the president and chief executive of the Professional Services Council, which represents 350 government contractors. CGI officials have publicly said that while their company created the system’s overall software framework, the Medicare and Medicaid agency was responsible for integrating and testing all the combined components.

There was so much of a political push to get it ready on time, that concerns for the technology seem to have been pushed aside:

But Mr. Chao’s superiors at the Department of Health and Human Services told him, in effect, that failure was not an option, according to people who have spoken with him. Nor was rolling out the system in stages or on a smaller scale, as companies like Google typically do so that problems can more easily and quietly be fixed. Former government officials say the White House, which was calling the shots, feared that any backtracking would further embolden Republican critics who were trying to repeal the health care law.

Marilyn B. Tavenner, the administrator of the Centers for Medicare and Medicaid Services, and Kathleen Sebelius, the secretary of health and human services, both insisted in July that the project was not in trouble. Last month, Gary M. Cohen, the federal official in charge of health insurance exchanges, promised federal legislators that on Oct. 1, “consumers will be able to go online, they’ll be able to get a determination of what tax subsidies they are eligible for, they’ll be able to see the premium net of subsidy,” and they will be able to sign up.

This is not an auspicious start for a government program that has to persuade people about the competency of government to regulate a huge portion of our economy, and an important aspect of personal lives.