Cognitive-behavioral therapy (CBT) has been reviewed and described as an empirically supported treatment for anxious youth. One component of CBT is the use of out-of-session "Show That I Can" tasks (STIC; i.e., homework tasks). STIC tasks vary in content and are to be completed between sessions. We discuss homework in CBT for Robert, a 13-year-old boy with social anxiety. Robert experienced distressing anxiety participating in and giving presentations at school and was fearful of open-ended questions. Robert had difficulty maintaining conversations with peers and reported being preoccupied with a concern that he would say something "weird" or "stupid." Robert avoided numerous situations, and his social anxiety affected his grades, social interactions, family, and quality of life. Robert's initial homework tasks entailed (a) journaling and self-monitoring anxious feelings and thoughts, and (b) practicing relaxation skills. During the second half of treatment, Robert's STIC assignments were exposure tasks, including (a) opinion discussion assignments, (b) participating in class, and (c) initiating conversations with children at the bus stop. The present discussion focuses on how homework was individualized and presented so that it was palatable and sensitive. Issues regarding out-of-session exposure tasks that elicit sufficient anxiety, resistance to high-level exposure tasks, and parent involvement are explored. (Contains 2 figures and 1 table.)