We get a lot of questions from small business owners about paying for their employees’ health insurance premiums. Many believe they can pay for employees’ health insurance premiums tax free. The reality is that as of July 1, 2015, employers are no longer allowed to reimburse employees for health insurance or pay for individual health insurance premiums. All healthcare premium payments must be paid through a group healthcare plan. Violations could result in a penalty of $100 per day per employee.