Hello @AlcaeusF, Appreciate your reply. If I setup a deduction (Taxable HSA), it will require me to pay SS/Med and Futa on the HSA contribution amount (As per the link you have provided). The HSA contribution for 2% shareholders should look exactly like the "S-Corp Owners Health Insurance" pay type. It should be FIT taxable but exempt from SS/Med and FUTA. Thanks.