In 2014, most individuals will be penalized for not having health insurance. In 2014, the penalty will be 1% of annual income or $95, whichever is greater. In 2015, the penalty will be 2% of annual income or $325. In 2016, the penalty will be 2.5 percent of your annual income or $695. You will pay a penalty when you file your taxes at the end of the year.