When she retired, my wife received a retiree benefit in the form of a 403b account with pre-tax dollars in it that can be used for any purpose, they can be healthcare costs or any other purpose as well. The dollars are taxed when they are withdrawn from the account. The 403b benefit was given to her replacing the benefit that she was originally going to receive for regular family healthcare coverage until she turns 65. We used this money to pay COBRA healthcare premiums (for a family plan so that my 24-year old non-dependent daughter is covered) in the final 6 months of 2019. Two questions - 1) To make adjustments and file our Wisconsin state income tax, can we claim the entire family plan healthcare premium for the six months? 2) Or can we only claim the amount we would have paid for health insurance if we were only covering my wife and myself?