Sometimes.

Other than being self-employed, all medical expenses need to be itemized if you want to count them towards non-taxable income. Always consult a tax professional first before making a decision on this.

Additionally, when itemizing, you are only able to deduct the amount of money that is spent greater than 7.5% of your adjusted gross income. For example, if your AGI is $50,000, the first $3,750 you spend towards health care will be taxed. Every dollar that you spend beyond that amount is tax deductible when itemized.

If you are self employeed.. #

And pay all of your health insurance premiums, those cost can be counted as a business expense. This is do-able as an ‘above the line’ deduction, so you will not need to itemize on Schedule A.

If you have employer-sponsored health insurance.. #

If you are a w-2 employee, you can only deduct the out-of-pocket portion of your employer-sponsored health insurance premiums only if you take the itemized deduction on your tax return. Even then, you can only deduct the cost that are over 7.5% of your AGI.

If you have a Marketplace plan.. #

If you are self-employed and have Marketplace plan, the above stipulations apply.

If you are not self-employed, all cost over 7.5% of your AGI can be deducted, not just your premiums.

Premium subsidies are never tax deductible. If your plan has a $1000 a month premium, but your subsidized cost is $250, you are only allowed to count the $250 towards the 7.5% threshold.

If you have COBRA.. #

COBRA premiums are tax deductible as a medical expense if you itemize and your total medical expenses exceed 7.5% of your AGI.