A communications server increases the value of cable and communication services by enabling the integration of packet network content with directed advertising in a managed environment. Such services may include Video On Demand and videoconferencing running on a Converged Communication Platform. Content processing within the server enables the combining of streaming content with different types of ads. Content integration is controlled through software negotiations between subscriber, advertiser, and content provider software agents. The rate, selection, placement, and number of advertisements within a television program or videoconference can also be determined. The ability to custom tailor content and advertisements increases the value of advertising, lowers costs to subscribers, improves the viewing experience, and disburdens transaction participants from the manual tasks that would otherwise be required during transaction setup.