The data, knowledge, inference, and reflective capabilities of expert systems are limited. We describe a collection of tools that address the problem that deception poses for expert systems and for organizations that employ them to reason about observations, plan, or make decisions. We have completed a Phase I SBIR in which we explore the ways that deception, of deceiving, and of the components of expert system. For Phase II we proposed to build a deception planner and use the deceptive plans to detect the weaknesses of particular expert systems and determine how they can be mitigated or eliminated. Specifically, our objective is to develop a collection of tools to suppon counter-deception reasoning in support of the situation assessment task for the Navy's Outer Air Battle mission. Our deception planning methodology calls for the deceiver to behave in a way that manipulates the beliefs that the target forms based on his (the deceiver's) emissions and actions. Our deception planner integrates case-based reasoning, sophisticated planning technology, and belief formation and revision technologies.