This is about USA where health insurance is mandatory for most people (with the exception of some groups) due to the Affordable Care Act and Patient Care and Coverage Act (aka Obamacare).
This question applies only to those States where people have to pay income taxes to the State and where the States enforce a penalty on a lack of health insurance.
Some States, such as Massachusetts, had mandatory health insurance already before Obamacare made the requirement nationwide. People who opted not to get health insurance in MA have had to pay a penalty to the State with the income tax.
Because of this, is it possible that a freelancer without health insurance could (at least in MA) end up having to pay a lack-of-insurance penalty separately to both IRS and to the State they file their taxes in?