Yes you can deduct premiums paid for medical insurance which includes the types of insurance described in Scruff_Curmudgeon's thorough answer. There is a relatively high threshold to get any tax benefit from medical expenses. Only the amount of unreimbursed medical expenses in excess of 7.5% of your Adjusted Gross Income can be deducted. Those deductible expenses along with all your other itemized deductions must add up to more than the standard deduction for you to get a tax benefit. TurboTax does the calculation for you after you have entered all your unreimbursed expenses. You won't know the result until you have entered all your income and all your itemized deductions. Many taxpayers who itemized deductions in past years are expected to get a better result from the standard deduction in 2018 since the deduction is now about double what it was last year.
