Abstract: A retail kiosk advertising system includes a retail display structure management server in communication with one or more retail display structures that support and display a retailer computing device and one or more consumer items for sale. The retail display structure management server receives proximity information from a proximity sensing device configured on the retail display structure in which the proximity information indicates when a portable computing device is within a specified range of the retail display structure. In response, the server determines an identity of a user of the portable computing device, obtains targeted advertising content associated with the consumer items, transmits the targeted advertising content to the retailer computing device. The retailer computing device also plays the targeted advertising for view by the user, and facilitates a transaction for the consumer item with the user.