🔥 DAILY TAX TIP #18 — S-CORP OWNERS: HEALTH INSURANCE MUST BE REPORTED CORRECTLY Short Story: A business owner proudly told me, “I run everything through my S-Corp, even my health insurance. It’s all deductible.”I said, “Show me where it’s reported on your W-2.”He blinked.When the IRS blinks back, it’s never friendly. THE TAX RULES:• If you are a more-than-2% shareholder in an S-Corp and the company pays your health insurance, it must be included in your W-2.• It is shown in Box 1 of the W-2 (wages subject to income tax), but not in Boxes 3 and 5 (Social Security & Medicare), when properly set up.• This allows the shareholder to potentially take a Self-Employed Health Insurance Deduction on Schedule 1, Line 17 of Form 1040.• Primary references: - IRS Notice 2008-1 - Publication 15-B (Employer’s Tax Guide to Fringe Benefits) - Instructions for Form W-2 and Form W-3 🧭 Quick Action: ✅ The S-Corp must either:• Pay the insurance premiums directly, or• Reimburse the shareholder in the same tax year. ✅ Add the total premiums to W-2 Box 1 as “Shareholder Health Insurance.” ✅ Do not include it in Social Security or Medicare wages (when correctly structured). ✅ Report the deduction on Schedule 1 of the shareholder’s personal return. WHY IT MATTERS: ⚠️ If not reported properly, the IRS can disallow the deduction entirely. 💰 Done correctly, the deduction reduces adjusted gross income, which may reduce taxable income across multiple categories. 🛡️ Proper reporting protects both the S-Corp structure and the audit trail. PRO TIP: Add a year-end checklist item: “Verify total health insurance paid for each >2% shareholder and confirm W-2 adjustment completed before filing. ”No scrambling. No regrets. BOTTOM LINE DRILL CALL: If the business pays your health insurance, your W-2 must say. No shortcuts. No silent reimbursements. Documentation + reporting = protection + deduction.