Subscribers request programs from a network based content server and view the requested programs via their customer equipment. The content server receives various programs and breaks the program content for each program into a sequence of program segments, which are logically linked by program association indicia. The content server also receives advertisements and stores the advertisements as advertising segments, which generally contain at least one complete advertisement, but the invention is not limited thereto. Upon receiving a program request from a subscriber, the content server will identify advertising segments to provide along with the program segments for the requested program, and where to place the advertising segments among the program segments. Next, the content server will generate composite association indicia identifying the sequence of program and advertising segments, and effect delivery of the program and advertising segments to the subscriber in the sequence defined by the composite association indicia.