A delivery service system and methods of use are described. The system and methods eliminate needs for a user to wait on a service provider's assistance to determine the cost of sending a package while protecting the service provider with prepayment before delivery. The processes described enable a new efficiency in package delivery wherein the users no longer need to wait in a queue at a delivery service and the delivery service no longer needs to have customer service representatives determining the cost to deliver the package and accepting payment from customers prior to the delivery service accepting the package. Such systems enable automated delivery of packages with minimal human intervention.