A method includes receiving, by a payment provide server of a payment provider from a point-of-sale (POS) device associated with a first merchant at a merchant location, a checkout request for a first user to purchase one or more items sold by the first merchant. The method further includes accessing an account of the first user with the payment provider based on authentication information included in the checkout request and identifying a previously stored payment token that is associated with the account of the first user, the previously stored payment token indicating one or more additional items for potential purchase. Further, the method includes in response to the identifying, transmitting instructions to the POS device that cause the POS device to display a request for the first user to add at least one of the one or more additional items for potential purchase for checkout at the merchant location.