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.