Retiree Medicare Premium Deduction for Business Owners

WSJ just alerted me to another tax provision of interest.

{{ Medicare premium deduction

“If you are a retiree who is self-employed, you can deduct your Medicare premiums even if you don’t itemize,” Koeppel says. This includes Medicare Part B and D, plus the cost of supplemental Medigap policies or the cost of a Medicare Advantage plan.

The IRS considers you self-employed for this deduction if you own a business as either a sole proprietor (Schedule C), partner (Schedule E), limited liability company member, or S corporation shareholder with at least 2% of the company stock. Other special rules apply. See the instructions on the 1040 form for details.

This tax benefit isn’t subject to the 7.5% of adjusted gross income test that applies to itemized medical expenses. (Under that rule, you can claim medical deductions for amounts paid for everything—from dental bills and doctor fees to nursing-home care—that exceed 7.5% of your gross income.) }}

I wonder if you can deduct IRMAA, too? For higher income retirees, that’s an even bigger number than the base Medicare premium.

Of course, you’d have to pay FICA taxes on that business income to qualify for the Medicare premium deduction. I’ve found that paying additional FICA to boost your SS benefit is still a reasonable deal as long as your AIME is below the 2nd bend point, but not above it. For someone paying max FICA starting in their mid to late 20’s, they’d likely reach the 2nd bend point by age 45 or so. Those soldiering on in the workplace beyond that are out of luck.


I wonder if anyone sells platinum plus plus plus medigap policies that could essentially enable business owners to deduct all, of most of, their medical expenses (by effectively wrapping them into the policy and making them exempt from the 7.5% AGI limitation)? Or are medigap policies regulated such that no such thing could exist.

Yes, it’s a premium, so it’s a qualified medical deduction.

There are other ways to get a tax advantage for Medicare premiums without having to be self-employed and paying self-employment taxes:

  • If you have an HSA, the premiums paid to Medicare (i.e. Part B, C, and D) are eligible HSA expenses, so you can take a tax-free withdrawal from your HSA to reimburse yourself for the premiums. Note: Premiums for Medicare supplement plans are not eligible HSA expenses
  • Medical insurance premiums, including those for Medicare, are eligible medical expenses for itemizing on Schedule A. Note: As already noted, only medical expenses in excess of 7.5% of your AGI can be deducted. Additionally, your total itemized deductions need to be more than your standard deduction for you to gain a financial advantage by itemizing. Under current law, this would become more likely in 2026 when the standard deduction returns to the prior rules.



Medigap policies are pretty strictly regulated. The supplement plan with the most comprehensive coverage for people turning 65 on or after Jan 1, 2020 is Part G. Part G covers most co-pays, co-insurance and out of pocket expenses, after paying the Medicare deductible. Those who turned 65 earlier and currently have Part F have slightly better coverage, since Part F covers the same things as Part G, plus covering the Medicare deductible. Neither of those supplements include prescription drugs, long-term care, dental or vision, since original Medicare does not cover any of those costs. Therefore, any of those costs would still have to go through as itemized deductions and be subject to the 7.5% AGI limitation.

Medicare Advantage plans often do cover prescription drugs, dental and vision, but are generally have significant co-pays, which would also be eligible for itemizing.