Getting the S Corp Health Insurance Tax Deduction Right

Navigating the s corp health insurance tax deduction can feel like a bit of a headache at first, but it's one of those perks of the tax code that really pays off if you handle the paperwork correctly. If you've recently made the jump from a sole proprietorship to an S Corp, you've probably noticed that things aren't as simple as they used to be. You're now both the employer and the employee, and while that comes with some great tax-saving opportunities, the IRS has some very specific hoops for you to jump through to make sure your health insurance remains a deductible business expense. ...

February 20, 2026 · 7 min · Pietro Haessler