The transtheoretical nature of fundamental dilemmas in contemporary psychotherapy is explored. The basic distinction between technical and ethical dilemmas in clinical practice is discussed, as well as the ramifications for the psychotherapist. Clinical dilemmas identified by survey research studies and interviews with master psychotherapists are reviewed. In addition to dilemmas relevant to circumscribed areas of psychotherapy, such as brief therapy, managed mental health care, sexual questions, feminist therapy, dilemmas fundamental to the psychotherapeutic process as a whole are examined. Finally, clinical examples are provided that include such issues as hospitalization of the suicidal patient, dealing with known contraindications, treating the intractable patient, and self-care of the psychotherapist.