Historically Video On Demand (VOD) advertising has required that programming content and advertising content be encoded and delivered together. In 2006, we deployed two field trials of “dynamic insertion,” the run-time assembly of advertising and programming content. This paper details the execution of these trials from an ad-server perspective. We explore the requirements of an ad-serving solution, on both the execution and reporting aspects of a campaign. Sections 1 and 2 provide introduction and background material. Section 3 details the technical requirements for campaign management and execution. Section 4 details the data that is reported on and best practices for its analysis.