What Is the Self-Employed Health Insurance Deduction? 06.06.2022 · The remaining deduction may not be lost—you can claim any premiums you can't deduct as self-employed health insurance as out-of-pocket medical expenses on Schedule A, Itemized Deductions. However, you'll have to itemize deductions to get a benefit, and you only get to deduct out-of-pocket medical expenses that exceed 7.5% of your adjusted gross income …