If you reported K1 activity on your return and reported an amount in Box 1, you claim the can claim the deduction in the follow up questions after entering your K1. It is in the screen that says Other Situations and in this screen you will check I personally paid health insurance and/or long-term care insurance premiums for myself and my family and this S corporation paid me wages.
I don't know how you entered this deduction because according to the instructions, you would have had to enter this either from a K1 or a Schedule C because you must have income to be eligible for the deduction from either a Schedule C or K1. I have a feeling you may have tried to enter this under Self-employment income and expenses and this is why the program is prompting you to upgrade.
If this was enter from the K1 screen, you would not be prompted to upgrade but again, you would need a K1 to report it.
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