“It’s really all over the board,” Greene-Lewis said. “It could be more medical devices, out-of-pocket expenses for prescriptions, or flying to a seminar about a condition you have.”
If you pay for health insurance with after-tax dollars, your premiums might be able to count toward that deductible. Expenses that are nondeductible include cosmetic charges, gym memberships and the like, as well as expenses for which you are reimbursed.
For the self-employed, the rules governing health insurance premiums are bit different. If you have a profit, you might be able to write off the premiums you paid for health, dental and long-term care insurance for you and your dependents.
Because the deduction for self-employment insurance is an adjustment to income, you don’t need to itemize to take advantage of it — although it does come with limitations. For instance, the value of the deduction cannot exceed your profit.
Additionally, whether self-employed or not, certain medical expenses come with deductibility limitations, including long-term care premiums (see chart below).