The negative therapeutic reaction can be used as a lens illuminating issues of psychoanalytic technique and therapeutic change. Its paradoxical development is examined within the context of current controversies involving the concepts of borderline personality organization and empathy. Negative therapeutic reactions are seen to reflect, among other failings, the failure of theory to “contain” dialectical tensions between self and other, subject and object, health and illness. Greater theoretical sophistication can point the way toward vigorous and more hopeful therapeutic engagement of these challenging reactions.