A computer-implemented system and method to facilitate a purchase utilizing a flexible spending account, comprising the steps of: receiving, at a host computer, a request for payment authorization for an item; determining whether the item qualifies for pre-tax treatment; and when the item qualifies for pre-tax treatment: determining at least partial payment authorization for the item, transmitting the at least partial payment authorization for the item to a point of sale device; causing the flexible spending account to be debited for at least a portion of the purchasing amount of the item based on the payment authorization; and debiting a non-flexible spending account for an item not qualifying for pre-tax treatment.