In one embodiment, a system and method for receiving itinerary information and user information for a reservation for a user where the user has opted to acquire lost item protection for use with at least part of the reservation; receiving a lost item notification from a computing device associated with a notifior, the lost item notification including at least notifior information and lost item information; retrieving itinerary information from the first database associated with the user when it is determined that the notifior information from the lost item report matches the user information stored in the first database; facilitating presentation of a list of one or more establishments associated with the retrieved itinerary information; and automatically generating and electronically transmitting a lost item report to the selected at least one establishment if it is determined that the establishment information is stored in the second database.