This chapter discusses contemporary issues in assessing psychopathology and personality with interview. We discuss types of interviews, how clients and clinicians approach an interview, and structured versus unstructured interviews. The structure of the interview is presented along with continuing concerns with official diagnostic systems. Issues that complicate the assessment process for personality disorders are discussed, including the base rate problem, the role of affective disorders, state versus trait assessment, the role of culture, the reliability of psychiatric diagnosis, the problem of diagnostic overlap, and comorbidities. Current findings on the reliability of structured clinical interviews are presented. While structured diagnostic interviews show acceptable reliability, their convergent validity with similar instruments and with self‐report instruments are only modest. This means that two similar instruments, be they structured interview or self‐report tests, may not result in the same diagnoses for a given patient. The chapter concludes with a discussion of computer‐assisted diagnosis and suggestions for the future.