A system and a method for assisting in the process of generating mailing communications and satisfying their requirements are provided. The system and the method allow customers or users to interact on a computer network, such as the internet, with a database to generate a communication with minimal time or effort expended such that the communication complies with requirements for delivery of mail by a special service. The system and method inform users of requirements of special mailing needs to effectuate delivery of, for example, a legal letter, allows users automatic delivery of a mailing requiring a special service and provides automatic transfer of fees associated with postage and services rendered.