When we were coming up on the doldrums of the December news cycle, I knew we could count on Obamacare to keep breaking down in new and spectacular ways. This time, there are a bunch of Iowans who think they’re being processed by Iowa’s Medicaid system, but they’re not:

Nearly 16,000 Iowans who tried to apply for coverage via the trouble-plagued federal health-insurance website are being told to apply separately through the state Department of Human Services.

The Friday afternoon announcement is the latest bout of bad news about the website, which is a key part of the Affordable Care Act.

The announcement affects people who entered their information into healthcare.gov and received a notice that they might qualify for Medicaid. The federal computer system was supposed to transfer their applications to a state computer system, but that transfer has been complicated by technical problems. The timing is critical, because the new insurance coverage is supposed to take effect on New Year’s Day, which is Wednesday.

That’s 16,000 low-income Iowans who spent hours getting through the system, thought they were successful, got a notice that they might be Medicaid eligible and that their applications were being taken care of by Iowa. But their applications can’t get to Iowa, of course. Because FAIL.

Iowa made the announcement about this snafu Friday, Dec. 27, when so many people are thinking about their insurance applications and whether they went through after being told they would. They’re also attempting phone calls and e-mails. The state hopes to have this worked out by Jan. 31 and says coverage would be retroactive as of Jan. 1, but a) I never count on anyone telling me they’re going to cover me retroactively and b) Medicaid-eligible Iowans aren’t the segment of the population that can easily drop money on a doctor’s appointment until the state gets its act together or they wouldn’t be Medicaid-eligible.

But there’s a whole other set of people in this cohort who may have been told they were Medicaid eligible and their stuff had been sent to Iowa, when in fact they are neither Medicaid eligible nor had their stuff been sent to Iowa. Those people— are you ready for this?— are going to be told to go back to the federal exchange after Iowa determines they’re ineligible. How might that go for them?

Jesse Patton, a West Des Moines insurance agent who has helped numerous clients sign up for coverage on healthcare.gov, said he was not surprised by Friday’s announcement. “I’m not happy about it,” he said. “For a lot of these people, I spent three or four hours to get them through the process, and now they’re back in limbo.”

What’s the root of the problem with this data transfer?

Aaron Albright, a spokesman for the Centers for Medicare and Medicaid Services, which is implementing Obamacare, said his agency is working with states to get them the information they need to determine whether applicants are eligible for public programs. He said federal officials have been sending information to states in something called a “flat file,” but he said not all states are accepting those.

McCoy, the Iowa human-services spokeswoman, said the flat-file format is different from what Iowa was told to expect. She also said many of the files Iowa has received from the federal system are missing crucial information, such as Social Security numbers and income reports.

Who could have predicted that the federal government would have trouble synching up all these computer systems to seamlessly interact in under a year in one of the biggest tech undertakings it had ever attempted?

The Washington Post piece assumes the federal data hub itself will work perfectly, even though it’s meant to cull an incredible amount of data and pair it with an incredibly complex set of eligibility requirements. I think even that’s an open question, but here’s the bottom line: This is a giant tech undertaking which will need to serve many localities with different needs, link existing technologies and personnel with a new, giant federal hub, and somehow make sure all of them work together to smoothly to guide consumers who have no idea what to expect in subsidies or services through a brand new web portal for health insurance. They have less than a year to accomplish this. It seems there has been no pilot program, no training, and no beta testing. This thing is ORCA on steroids.

Oh, and there’s a 30-60 day public commenting period before HHS even finalizes the rules it proposed Tuesday. So, make it nine months to implementation. Here’s hoping.

A little over a year later:

Some 4 million people lost health coverage due to cancellation, according to Associated Press coverage. The Obama administration reversed course and said these substandard plans could exist for another year, but not all states and insurers agreed to this fix.

That means it’s possible the United States is entering the first year of Obamacare with a net loss of 2 million insured, according to the law’s critics.

But anyone worried about their insurance coverage can just call a number (nope) or visit someone in person (nope) or be assured that the federal website transferred your info (a thousand times nope), or be satisfied that Michelle Snyder is hanging out at the bar with Lois Lerner and the rest of Obama’s well-paid forced retirees in charge of national Charlie Foxtrots, and they all have insurance (yep).