This contribution delineates the formal and dynamic characteristics of generosity. It traces the origins of the trait of generosity to a complex interplay of hard-wired capacities for concern and altruism with gratifying experiences of early infancy and identifications with the generative parental qualities during later childhood and adolescence. Five pathological syndromes (namely, unrelenting generosity, begrudging generosity, fluctuating generosity, controlling generosity, and beguiling generosity) seem to exist in this realm. Technical implications of the notions outlined in this paper include: (i) having and maintaining an attitude of generosity towards the patient, (ii) listening and intervening with an attitude of generosity, (iii) recognizing and accepting the patient's healthy generosity, (iv) diagnosing and interpreting the patient's pathological generosity, (v) unmasking and interpreting defenses against generosity, and (vi) discerning and utilizing the countertransference to generosity. The paper also touches briefly upon miserliness, the opposite of generosity, and upon sociocultural dimensions of the matters involved.