Two weeks ago, 34-year-old Leah Beth Brummett heard that question while getting her taxes done at a Jackson Hewitt office in Houston, and thought "it seemed kind of weird to me to mix taxes and your health insurance."
"But it worked out for me," said Brummett, a student and website sales employee who after a decade of going without health insurance signed up at Jackson Hewitt's suggestion with GetInsured that day. She enrolled in an Obamacare plan with a sticker price of $280 per month—but after government subsidies, she'll pay about $28 per month for coverage.
"It was awesome," Brummet said of the short amount of time it took to shop and enroll.
Tax filing season may be the ideal time for buying insurance because about 75 percent of U.S. filers are getting a refund—an average of $3,000 per family—and thus may have money to spend on their first month's premium, Haile said.
"They're cash flush," said Haile, whose firm has 4,000 storefront locations and a presence in 2,600 Wal-Mart stores. And people get in the mindset of "thinking about future spending" when they have their taxes done, he said.
But there is another major reason for tax preparers to focus on Obamacare. Under the health-reform law, the penalty for failing to have some kind of health insurance by March 31 is the greater of $95 or 1 percent of a person's annual adjusted gross income. That penalty will be deducted from whatever tax refund is eligible for next year, and in future years.
(Read more: Obamacare hits 4 million sign-ups as bar lowers )
Despite all the headlines about Obamacare, Haile said, "99 percent of our customers are confused." They are either unaware that the individual mandate to have insurance begins this year, or mistakenly believe $95 is the most they will pay in penalties, he said.
"Most people will pay considerably more," said Haile, adding that the threat of a penalty is a big motivator to sign up.
He said a customer's tax return gives Jackson Hewitt "90 percent of the information we need to complete the application" for Obamacare insurance, which is sold through government-run exchanges. And the average time to get a customer through the application process was just 6.1 minutes as of Wednesday, Haile said.
"People are eager to kill two birds with one stone—it's great piece of mind for people to have both their taxes and health insurance taken care of in one fell swoop," said Chini Krishnan, co-founder and CEO of GetInsured.
Jackson Hewitt refers clients eligible to buy Obamacare from an government-run exchange to Getinsured or tells them how to complete the process at home. Jackson Hewitt also will help enroll customers if their income qualifies them for the government-run Medicaid and CHIP health coverage programs, which serve lower-income adults and children, respectively.