A system which facilitates the purchase of an item qualifying for pre-tax treatment utilizing at least one flexible spending account (FSA). A host computer may receive a request from a point of sale (POS) device to authorize payment for one or more items. The host computer may process the request to determine if the item qualifies for pre-tax treatment. If the item qualifies for pre-tax treatment, the host computer may transmit payment authorization to the POS device and debit at least one FSA and/or at least one non-FSA account.