Level 15

If the health insurance premiums are paid by the S corp for the shareholder, that makes it a taxable event for the shareholder through payroll, except you don't need to do income tax withholding on it. That's because the shareholder then gets to include it as an income deduction. The S corp will see it as part of Gross Payroll, or this portion is a Taxable Fringe Benefit.

You never get to take it as Health Insurance Premium deduction in both places. That is what is meant by "cannot Double Dip."

Who did the payroll for this S corp? Is this your S Corp? Is that W2 yours? You keep using First Person for asking this question.

Whose tax return(s) are you working on?

"Level Up" is a gaming function, not a real life function.
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