Flyboy - did you happen to see the last 2 posts in the thread you mention: http://benefitslink.com/boards/index.php?/topic/56028-tax-free-premium-reimbursement-s-corp-loophole/ Others of us disagree w/ your conclusion. I remain of the opinion that 2% s-corp shareholders are entitled to the SE health insurance deduction on their personal 1040. But only if it is paid for with after-tax dollars by the s-corp and reported as taxable income on the individuals W-2. The deduction on 1040 is a dollar for dollar reduction of AGI, meaning it is effectively equivalent in individual income tax savings. Because the s-corp pays it with after-tax dollars, it avoids the health reform prohibition on pre-tax reimbursement of individual premiums. See post #5 in the linked thread for relevant quotes from Notices 2008-1 and 2013-54.