The invention is a computer-implemented method and system to facilitate a purchase utilizing a tax-advantaged account. A request for payment for an item is received from a requester. A determination is made whether the item qualifies for pre-tax treatment. If the item qualifies for pre-tax treatment at least a partial payment amount for the item is determined. The tax-advantaged account is debited for at least a portion of the purchasing amount of the item based on the payment authorization; and the at least partial payment amount for the item is transmitted to an account of the requestor.