A major issue in many domains is to present information to people that is tailored to their need, in such a way that it supports them in their tasks. In this paper, we present the Virtual Document Planner (VDP), a platform we developed for generating tailored interactive multimedia presentations in the surveillance domain. Integrated with the surveillance operators’ graphical interface, the VDP provides tailored information delivery mechanisms that adapt the operators’ information rich environment to their tasks and information needs. Categories and Subject Descriptors H.5.2 [User Interfaces]: Natural Language, Graphical User Interfaces; H.5.3 [Group and Organization Interfaces]: Synchronous Interaction; I.2.7 [Natural Language Processing]: Discourse, Language Generation. General Terms Design, Human Factors. Keywords Tailored information delivery, multimedia presentation generation, discourse approach, task-sensitive user interface.