The increasing number of characterologically difficult patients in psychiatric practices has produced a plethora of theoretical formulations, treatment strategies and techniques. The major shifts in theoretical emphasis from drive theory to object relations theories and self-psychology has encouraged many psychiatrists to treat these patients in psychotherapy. The heterogeneity and variability of clinical profiles represented in this group of patients, however, still prevents prescription of "the" treatment of choice for this patient population. A major focus on treatment considerations in this paper is the assessment process with emphasis on determining the capacities for inter-personal relationships, psychological mindedness, empathy and psychological soothing of self and others. The advisability of establishing a "contract" as a prerequisite to treatment is suggested as an important factor in determining outcome. Other particular treatment issues are addressed such as frequency of sessions, "secrets", premature provocation of intense affect, medications, consultations, hospitalization, self-mutilation, substance abuse and indications for termination. The complex vissicitudes of the transference and countertransference processes with this group of patients is pointed out especially those feelings of helplessness and range sometimes experienced in the counter-transference. Long term intensive psychotherapy with many of these patients probably still belongs to the area of therapeutic heroics. Hard evidence for good and poor outcome is scarce and therapeutic zeal is too often based on anecdotal testimonial from adherents of one approach or another.