The Obama administration promised to have the Obamacare website working smoothly by Saturday, but even President Obama knows this latest deadline is another target that his team is likely to miss.

Only about 25,000 Americans were able to enroll on the federal government’s HealthCare.gov website in October, when most people instead encountered computer errors. And although Mr. Obama and his top advisers vowed to fix the problems by the end of November, they have retreated from that pledge in favor of a scaled-back promise by Health and Human Service Secretary Kathleen Sebelius that the website will be working for “most users” by Saturday’s deadline.

This week, administration officials acknowledged they are holding back on a marketing campaign for the program because they don’t want too many users to visit the flawed site. And HHS also revealed this week that the Spanish-language version of HealthCare.gov still isn’t ready to enroll people; HHS is postponing that service again until sometime in December.

The administration also Wednesday announced another major delay, putting off by one year the online program that lets small businesses shop for plans through the federal Obamacare marketplace.

The developments are the latest in a series of downsized goals, broken promises and delays for Obamacare since the program became law of the land in 2010. If there has been a hallmark of Obamacare so far, it has been watching Mr. Obama’s optimistic assurances crumble later under the weight of reality.

“The administration completely oversold what it was going to be, in terms of all dessert and no spinach,” said Paul Howard, a specialist on health-care policy at the nonprofit Manhattan Institute.

Throughout the president’s re-election campaign in 2012, Mr. Obama trumpeted the signature achievement of his first term and told voters that he was trustworthy above all else.

“You do want to be able to trust your president,” Mr. Obama told supporters in Ohio a few days before Election Day. “You want to know that your president means what he says, and says what he means. And after four years as president, you know me. You know where I stand. You know I tell the truth.”

Those words stand in stark contrast to Mr. Obama’s now-infamous broken pledge, repeatedly made without qualification, that “if you like your health-insurance plan, you can keep your plan.” By last month, with more than 3.5 million people being forced out of their old insurance policies by Obamacare, the president admitted that his promise wasn’t true for many people.

Behind the scenes, he reportedly berated his staff for allowing him to boast in public that buying health insurance would be as easy as shopping on Amazon.com.

In an interview with Barbara Walters to be broadcast Friday night on ABC’s “20/20” show, Mr. Obama said his team is looking into why he was kept in the dark about the website’s problems.

“We’re evaluating why it is exactly that I didn’t know soon enough that [it] wasn’t going to work the way it needed to,” Mr. Obama said. “But my priority now has been to just make sure that it works.”

But even the president’s apology was a bit of misdirection. Mr. Obama knew as early as February 2010, one month before he signed the law, that millions of Americans wouldn’t be able to keep their health insurance.

At a health care summit with congressional Republicans at Blair House on Feb. 25, 2010, House Majority Leader Eric Cantor, Virginia Republican, who was House minority whip at the time, voiced concern to the president that “between eight million and nine million people may very well lose the coverage that they have because of the construct of this bill.”

“I don’t think you can answer the question in the positive to say that people will be able to maintain their coverage, people will be able to see the doctors they want, in the kind of bill that you are proposing,” Mr. Cantor told Mr. Obama.

The president replied that a relatively small portion of the population would be affected, and they would be better off under Obamacare.

Mr. Obama told Mr. Cantor, “The eight to nine million people you refer to that might have to change their coverage — keep in mind out of the 300 million Americans that we are talking about — would be folks who the Congressional Budget Office estimates would find the deal in the exchange better. So, yes, they would change coverage because they got more choice and competition.”

Those promises, Mr. Howard said, “were papered over” later with regulations requiring more expensive coverage for many.

“The administration had to require tight grandfathering of current plans to move people into the exchanges, which means cancellations,” Mr. Howard said.

Within six months of his second inauguration, Mr. Obama had broken his own law, delaying the crucial employer mandate portion of Obamacare by a full year until 2015. The administration cited confusion by businesses about how to report employee insurance information to the Internal Revenue Service.

The president told supporters in Southern California this week that he’ll never back down from making sure the law works.

“We are going to continue to implement the health care law,” Mr. Obama said. “The product is good. People want it. And we should not live in a country where people are going bankrupt just because they get sick. And anybody who is going to keep on pushing against that, they will meet my resistance, because I am willing to fix any problems that there are, but I’m not going to abandon people to make sure that they’ve got health insurance in this country.”

With the faulty website preventing many people from enrolling, health care analysts say the next problem for Obamacare could be the failure to bring young, healthy people into the program. Obamacare needs people who don’t require much medical care to still be paying premiums, to offset the costs of older, sicker people who place greater demands on the system.

“They have assumed wrongly that the plans they’re trying to sell through the exchanges are going to be attractive to relatively healthy Americans,” said James Capretta, a public policy specialist at the right-leaning American Enterprise Institute. “I just think that’s wrong. Lots of people are going to end up not buying those plans. Mainly it’s going to be an attractive place for people who have existing health problems. It’s going to become essentially a program for relatively less healthy people.”

Mr. Howard predicted the trend will create more problems for the program, financial and political, in 2014 as congressional mid-term elections near.

“If the picture doesn’t improve in terms of getting these young and healthy people to enroll and it stays skewed, you’re looking at a cycle where we’re going to have more expensive rate increases for 2015,” Mr. Howard said. “The government can push back [against insurers] and say the rates need to be lower, but the insurers can say ‘We’ll walk.’ That’s the real tension here.”

As this happens, the premiums for everybody in the system then have to increase, which makes buying insurance an even less rational act for a healthy person, which means even fewer will sign up, and on and on — a phenomenon analysts of insurance markets refer to as the “death spiral.”

“The expectation was that there would be a big pool of really healthy people offsetting a relatively smaller pool of more expensive patients. If that doesn’t play out, then the exchanges are looking at a problem in terms of affordability, a very serious problem,” Mr. Howard said.

While the Obama administration is saying the website is getting better, the problems might also be preventing younger, healthier consumers from finding out how truly expensive their coverage would be.

“Right now, people haven’t been able to really shop effectively,” Mr. Howard said. “A lot of these plans are going to be very narrow networks and come with high deductibles. Except for a few states you can purchase a plan and not really understand what kind of physician and hospital coverage you’re going to get. And then I would expect lots of stories to start popping up after January when people start to use the coverage and hearing complaints that they can’t see the doctor they want.”

Administration officials say the website should be able to handle 50,000 users simultaneously by Friday, citing steady improvement in the speed of the site. By last week, the average load time for the website’s pages was less than one second, down from October’s time of eight seconds, according to the Centers for Medicare & Medicaid Services.

Jeffrey Zients, who was tapped by Mr. Obama to troubleshoot the problems with the website, has warned that Saturday’s deadline will not be “a magic moment” for the site. Instead, he said it will continue to make steady improvement.

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