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I have the same question for tax year 2020.   I have a large one time Membership payment that is for "Lifetime Care - Advance Payments" as defined in IRS Pub 502.   I know this is unusual and perhaps I just can't use TurboTax this year.   There is no question that covers this under Medical expense deductions.   Can I somehow force entries into 1040 schedule A, overriding the system?   This is NOT regular Long Term Care insurance.    This is an advance payment in return for a contractual obligation to pay our medical expenses for life.

     In your answer below, you have identified the right item, but your hint about the search function seems to just bring me back to the standard questions.  What question can I used to input the amount I paid?    It is not one of your usual items.