We found 10 instances after the law was signed when Obama made the pledge again.
In remarks in Portland, Maine, on April 1, 2010, Obama said that "if Americans like their doctor, they will keep their doctor. And if you like your insurance plan, you will keep it. No one will be able to take that away from you. It hasnÂ’t happened yet. It wonÂ’t happen in the future."
After the U.S. Department of Health and Human Services issued regulations for the law on June 14, 2010, HHS Secretary Kathleen Sebelius blogged: "The bottom line is that under the Affordable Care Act, if you like your doctor and plan, you can keep them."
Obama then repeated the remarks during several campaign events in 2012, as well as at the first presidential debate in Denver on Oct. 3, 2012: "If you've got health insurance, it doesn't mean a government takeover. You keep your own insurance. You keep your own doctor. But it does say insurance companies can't jerk you around."
Finally, as recently as a few weeks ago, Obama was playing down the impact.
"Now, let’s start with the fact that even before the Affordable Care Act fully takes effect, about 85 percent of Americans already have health insurance -– either through their job, or through Medicare, or through the individual market," he said in a speech in Largo, Md., on Sept. 26. "So if you’re one of these folks, it’s reasonable that you might worry whether health care reform is going to create changes that are a problem for you -- especially when you’re bombarded with all sorts of fear-mongering. So the first thing you need to know is this: If you already have health care, you don’t have to do anything."
Overall, we didnÂ’t find one instance in which Obama offered a caveat that it only applies to plans that hadnÂ’t changed after the lawÂ’s passage.
Politifact; Pants on Fire: Barack Obama says that what he'd said was you could keep your plan 'if it hasnÂ’t changed since the law passed'