Is Your Health Insurance a Write-Off?

The deduction most owners underuse

If you’re self-employed and paying for your own health coverage, you may be able to deduct 100% of your premiums — medical, dental, vision, even Medicare premiums once enrolled — with no itemizing required. But how you claim it depends entirely on how your business is set up.

The rules that trip people up

• S-Corp owners: premiums must run through payroll and appear on your W-2 — skip that step and the IRS position is no deduction at all.
• Spouse has coverage at work? Any month you were merely eligible for that plan is disqualified — even if you never enrolled.
• Loss year? The deduction can’t exceed business profit, though excess premiums may still count as itemized medical expenses.

What’s in the guide

A plain-language table of who qualifies and where it’s claimed — sole proprietor, partnership, or S-Corp — plus the fixes if you’ve been doing it wrong.

Questions about how this applies to your business? Book a free discovery call — thirty minutes, no cost, no jargon. Or head back to all free resources.