This chapter addresses the challenges that counseling students may encounter in clinical practice situations that require complex case conceptualization skills. Topics to be explored include elements of comprehensive clinical assessment, such as objective testing, structured and unstructured interviews, and symptom-specific tests, as well as techniques for assessing clients' potential for self-harm or harm to others. The chapter examines the benefits and risks inherent in the process of diagnosing individuals presenting for treatment, along with the clinical tensions that often exist between the needs of clients and the requirements of the mental healthcare system. It begins with learning objectives based upon the following Council for Accreditation of Counseling and Related Educational Programs (CACREP) standards: 2F5.b, 2F5.g, 2F5.h, 2F7.a, 2F7.b, 2F7.b, 2F7.c, 2F7.e, 2F7.j, 2F7.k, 5C1.c, 5C3.a (CACREP 2016) and 2G5.c, 2G5.d (CACREP 2009) and continues with the subject matter. It then explores future needs for counselor programming.