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Medical, including insurance premiums, are entered on Schedule A.
Medical, dental, and vision expenses are reported on Schedule A and entered in the Deductions & Credits section:
You will then be prompted to enter your medical expenses, starting with prescriptions.
If you're using Free Edition and your medical expenses are large enough that you would benefit from itemizing deductions, you'll be prompted to upgrade to Deluxe, as Free Edition doesn't handle Schedule A.
@ColeenD3 is exactly right. But I will also point out that that total of all of your medical expenses (not just supplemental premiums but medicare premiums taken out of social security and out of pocket expenses (co pays, uninsured dental, etc.) must be more than 7.5% of your adjusted gross income. (So if you make $100k and have $8k in medical expenses the deduction is only $500. If you had $7k in medical expenses there would be no deduction at all.)
Additionally you have to itemize, which very few people do (<12%) because the standard deduction is so large. (For > 65 yrs old, single it is about $13.5k)
So I would certainly put in all of your medical expenses and let TT see if it helps. But don't have high expectations. It usually won't matter.
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