Health Insurance Options for S-Corp Owners and Their Employees

Health insurance is one of the few remaining benefits an S-Corporation can deliver with real tax efficiency. It is also the one that small S-Corps get wrong most consistently — usually because of a single assumption that is exactly backwards.

The assumption is that an owner who works in the business is an employee for benefit purposes. For fringe benefits, the Internal Revenue Code says the opposite, and nearly every rule below follows from that one reversal.

The Rule Everything Else Follows From

A 2-percent shareholder under § 1372(b) is anyone who owns more than 2% of the outstanding stock, or stock with more than 2% of the voting power, on any day of the tax year — counting stock owned constructively under § 318. That attribution matters more than most owners realize: a spouse, child, parent, or grandparent who works in the business is treated as a 2-percent shareholder even if they hold no stock in their own name.

The consequence is direct. § 106 excludes employer-provided health coverage from an employee's income, but as Notice 2008-1 puts it, "a 2-percent shareholder is not an employee for purposes of § 106." So the premiums "are not excludible from the 2-percent shareholder-employee's gross income under § 106," and the shareholder "is required to include the amount of the accident and health insurance premiums in gross income under § 61(a)."

An owner's health insurance is not tax-free at the company level. It is made whole on the personal return instead — but only if the mechanics are right.

Who Actually Gets Tax-Free Coverage

It is worth separating the two populations, because the draft version of this question usually blurs them:

• Employees who are not 2-percent shareholders — including a shareholder at or under 2% — get the ordinary § 106 exclusion. Company-paid premiums are tax-free to them and deductible by the corporation. Nothing unusual applies.
• More-than-2% shareholder-employees — and their attributed family members — do not. Their premiums run through W-2 wages and are recovered under § 162(l).

The Owner's Route: W-2 Inclusion, Then an Above-the-Line Deduction

Premiums paid or furnished by an S corporation for a 2-percent shareholder in consideration for services are "treated for income tax purposes like partnership guaranteed payments under § 707(c)" (Rev. Rul. 91-26). The sequence that makes this work:

1. The S corporation pays or reimburses the premiums and deducts them as a business expense under § 162(a).
2. The amount is included in the shareholder's Form W-2, Box 1 — but, per the IRS guidance on S corporation medical insurance, "not included in Boxes 3 and 5." It is not subject to Social Security, Medicare, or FUTA taxes where the § 3121(a)(2)(B) requirements are met and the plan or system provides for all or a class of employees (see also Ann. 92-16).
3. The shareholder reports the amount as income on Form 1040 and claims the § 162(l) above-the-line deduction, computed on Form 7206.

"Established by the S Corporation" — the Two Ways That Work

This is where the money is lost. Notice 2008-1 states that a plan is established by the S corporation if either:

1. "the S corporation makes the premium payments for the accident and health insurance policy covering the 2-percent shareholder-employee (and his or her spouse or dependents, if applicable) in the current taxable year"; or
2. "the 2-percent shareholder makes the premium payments and furnishes proof of premium payment to the S corporation and then the S corporation reimburses the 2-percent shareholder-employee for the premium payments in the current taxable year."

The failure case is Example 1: the shareholder obtains the policy and pays for it personally, and "the S corporation makes no payments or reimbursements with respect to the premiums." Result — "a plan providing medical care for shareholder A is not established by the S corporation and shareholder A is not entitled to the deduction under § 162(l)." Not a reduced deduction. None.

The W-2 step is equally load-bearing: the S corporation "must report the accident and health insurance premiums paid or reimbursed as wages on the 2-percent shareholder-employee's Form W-2 in that same year." Miss the December payroll entry and the deduction goes with it.

Two useful footnotes. Where a prior year was handled wrong, Notice 2008-1 permits timely amended returns marked "Filed Pursuant to Notice 2008-1" at the top. And paying only the owner's premiums does not endanger the S election — the IRS "does not consider payments of accident and health insurance premiums by an S corporation on behalf of 2-percent shareholder-employees to be distributions for purposes of the single class of stock requirement of § 1361(b)(1)(D)."

Two Limits That Can Cap or Erase the Deduction

Where QSEHRA and ICHRA Fit — and Where They Do Not

Reimbursement arrangements are widely recommended to small S-Corps, and they are genuinely useful — for the staff. They do not work for the owner.

If a QSEHRA does fit your team, the constraints are specific:

• Only an employer that offers no group health plan to any employee is eligible (§ 9831(d)(3)(B)(ii)). Setting up a group plan ends QSEHRA eligibility.
• It must be provided, not merely offered, on the same terms to all eligible employees; employees cannot waive participation.
• For tax years beginning in 2026, total payments and reimbursements cannot exceed $6,450 for self-only coverage or $13,100 for family coverage (Rev. Proc. 2025-32, § 4.63).

Common Mistakes

• Treating owner premiums as tax-free because the company paid them — § 106 does not apply above 2%.
• Buying and paying for the policy personally with no company payment or reimbursement, which forfeits the deduction entirely.
• Reimbursing in one tax year but reporting on the next year's W-2, or omitting the W-2 entry altogether.
• Putting the premiums in Boxes 3 and 5 and paying Social Security and Medicare tax that was never owed.
• Setting up a QSEHRA or ICHRA expecting the owner to benefit.
• Overlooking § 318 attribution for a spouse or child on the payroll.
• Running a salary too low to absorb the premiums under the earned-income limit.
• Missing that a spouse's employer coverage disqualifies the deduction month by month.

Practical Sequencing for Contractors

Most contracting S-Corps start owner-only or with a very small crew. At that size, a formal group plan is rarely practical and the individual-policy-plus-reimbursement route under Notice 2008-1 usually is — provided the reimbursement and the W-2 entry happen in the same year.

As the crew grows, the calculus changes: a group plan gives the staff a clean § 106 exclusion and the owner keeps the same § 162(l) treatment either way. That is the point to compare a group plan against an ICHRA on cost and administration — and to remember that adding a group plan closes the QSEHRA door.

How KDM Accounting Services Can Help

At KDM Accounting Services we help Florida contractors and S-Corp owners get this structure right and keep it right:

• Review how premiums are currently paid, reimbursed, and reported
• Set up the payroll entries so Box 1, Box 3, and Box 5 are correct before year-end
• Confirm the plan is "established by the S corporation" under Notice 2008-1
• Test the earned-income and subsidized-plan limits against your actual salary and household facts
• Coordinate with your insurance or benefits advisor on group, ICHRA, or QSEHRA design
• Keep compensation and benefits consistent with the rest of your S-Corp tax position

Get the Structure Right Before December

Almost every failure mode here is a timing failure. The reimbursement has to land in the tax year, and the W-2 entry has to land with it — which makes the final payroll run of the year the real deadline, not the April filing date.

If you are not certain your premiums are being reported correctly, or you are weighing coverage for yourself or your team, contact KDM Accounting Services. We will walk the current setup, fix what is off, and document it so it holds.