/Tax Strategy

Most business owners are leaving significant tax savings on the table.

How to Deduct Health Insurance Premiums as a Business Owner

Christine Kieffer February 5, 2026 6 min read

The self-employed health insurance deduction is one of the most valuable tax benefits available to business owners — and one of the most underutilized. If you are paying health insurance premiums out of pocket and not deducting them correctly, you are leaving real money on the table every single year.

This article breaks down exactly how the deduction works, who qualifies, and how to layer it with HSA contributions and advanced benefit structures to maximize your tax efficiency.

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