This chapter examines deeper into how assessment is used in adventure therapy. The original GRABBS model acronym is also covered as a microassessment of the moment-to-moment calculation(s) the adventure therapist conducts in order to adjust the experiences to further generate and evaluate information for accuracy. Group members project a representation of their behavior patterns, personalities, structure, and interpretation onto the adventure activities because they are typically unfamiliar with what is being asked of them in the experience. Goal setting is a critical practice of adventure therapy. Knowing the client’s goals, and ideally co-creating goals that both the therapist and client agree to, are important in knowing how progress toward the outcomes is being achieved. Using a nonconfrontational approach, the adventure therapist was able to relate to Bobby in a positive way and lessen further walls of resistance. Bobby’s social history profile included being kicked out of two structured military schools, his gang appearance, and negative behavior.