Turbtotax for Business - Medical Insurance for Officers

It depends. For a Partnership, these payments are considered Guaranteed Payments. Per IRS Instructions for Form 1065 Line 10 Guaranteed Payments: "Also include on line 10 amounts paid during the tax year for insurance that constitutes medical care for a partner, a partner's spouse, a partner's dependents, or a partner's children under age 27 who aren't dependents."

For an S-Corp, these payments are reported as Officer Compensation (also reported on Form W-2). Per IRS Instructions for Form 1120S Line 7. Compensation of Officers and Line 8. Salaries and Wages: "Include fringe benefit expenditures made on behalf of officers and employees owning more than 2% of the corporation's stock. <snip> Report amounts paid for health insurance coverage for a more-than-2% shareholder (including that shareholder's spouse, dependents, and any children under age 27 who aren't dependents)…"