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Mental health activities conducted by patients between therapy sessions (or "therapy homework") are a component of addressing anxiety and depression. However, to be effective, therapy homework must be tailored to the client’s needs to address the numerous barriers they encounter in everyday life. In this study, we analyze how therapists and clients tailor therapy homework to their client’s needs. We interviewed 13 therapists and 14 clients about their experiences tailoring and engaging in therapy homework. We identify criteria for tailoring homework, such as client skills, discomfort, and external barriers. We present how homework gets adapted, such as through changes in difficulty or by identifying alternatives. We discuss how technologies can better use client information for personalizing mental health interventions, such as adapting to client barriers, adjusting homework to these barriers, and creating a safer environment to support discomfort.