Tax Year Prior to 2020: Retiree after-tax contributions for health insurance

[Tootsie100254]

 I receive retiree medical benefits from my former employer. After-tax contributions for medical and dental coverage are deducted from my monthly pension payment. Are my contributions deductible on my 2019 federal return and my 2019 WI state return? 

[VictorW9]

Yes for federal, your premiums for both medical and dental are deductible. According to my understanding, you can still deduct after tax medical premiums for Wisconsin However, for 2018 your out of pocket costs subject to the 7.5% threshold of AGI were not deductible but are now deductible for 2019.

[PTP1]

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  The dollars are taxed when they are withdrawn from the account.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 covering my wife and myself?  

[BillM223]

I want to make sure that I understand - when the money is distributed to you, it is taxable income, right? If so, good.

The Wisconsin instructions say that you can deduct premiums paid for " “Medical care insurance” (which) means a medical care insurance policy that covers you, your spouse, and dependents..." See page 18 at here.

Thus, on the surface, it appears that you will have to break out the portion of the premium that applied to your non-dependent daughter.