Narcissistic personality disorder (NPD) is one of the most challenging clinical syndromes to treat in psychotherapy, especially due to the difficulties of establishing a good enough therapist–patient relationship. Countertransference responses to NPD can be particularly intense, frustrating, and difficult to manage, as is often reported in the clinical literature though not clearly supported empirically. The aims of this study were to (a) investigate the relationship between patients’ NPD and therapists’ responses; (b) examine the associations between patient, clinician, therapy variables and clinicians’ reactions during treatment of NPD patients; and (c) provide an empirically derived portrait of countertransference with NPD. A sample of psychiatrists and clinical psychologists (N = 67) completed the Therapist Response Questionnaire to identify patterns of countertransference, the Shedler–Westen Assessment Procedure-200, and the Global Assessment of Functioning Scale to assess the personality pathology and psychosocial functioning of a patient in their care. The results showed that NPD was positively associated with hostile/angry, criticized/devalued, helpless/inadequate, and disengaged countertransference and negatively associated with therapists’ positive response, regardless of patients’ personality and psychosocial functioning. NPD patients with stronger traits of cluster B personality pathology tended to elicit more negative and heterogeneous countertransference reactions than NPD patients without these features. The countertransference patterns with NPD patients were not strongly influenced by the variables of clinicians and therapy, with the exception of clinical experience. Overall, the portrait of therapists’ reactions to NPD provided a clinically nuanced and empirically founded description strongly resembling theoretical–clinical accounts. The therapeutic implications of these findings were discussed.