The irony of running a tabletop exercise, let alone one designed to introduce randomness and variable outcomes based on decisions, is that the exercise itself is full of unknowns. From scheduling conflicts to plans not being followed, to new information being introduced during the exercise, to participants making a decision that wasn't accounted for as part of the planning of the exercise, there will always be some sort of hurdle to overcome. In this chapter, we will look at some of these potential roadblocks and provide some strategies to deal with them to avoid derailing the entire exercise.