Abstract: A method is disclosed for facilitating the generation of highly personalized communications, such as newsletters, for a specific recipient. The communication's content is determined by and format is arranged according to software-controlled rules called “Content Directives”. Information about the recipient is recorded in a database and is reviewed to determine such things as whether a given recipient is to receive a given communication and what communication content should be sent to each recipient. Communications may be sent physically or electronically, and according to a flexible schedule determined either by the sender or by recipient.