This chapter addresses common clinical issues that Interpersonal Psychotherapy–Adolescent Skills Training (IPT-AST) group leaders have encountered. These issues include absences, engaging reluctant adolescents in group activities, difficult or defiant adolescents, breaches to confidentiality, challenging family situations, sensitive topics, and crises, including disclosures of suicidal thoughts and suspected abuse. The chapter discusses ways that the authors have addressed these common clinical situations in IPT-AST groups. Examples for addressing these situations are provided.