In this article, we provide an overview of our research program on therapeutic impasses and alliance ruptures. Beginning in the mid-1980s at the University of Toronto, and continuing in New York at Beth Israel Medical Center since the early 1990s, we have focused our efforts on trying to illuminate the processes associated with resolving ruptures in the alliance and working through therapeutic impasses. Influenced both by the relational turn in psychoanalysis and findings emerging from our own research on the process of change, we have developed and evaluated an approach to short-term treatment that appears promising. We are also developing and evaluating the effectiveness of training methods for enhancing therapists’ capacities to work constructively with negative therapeutic process, regardless of the particular “brand” of treatment they are practicing. Finally, we summarize some preliminary findings regarding the impact of therapists’ capacity for mentalization on both treatment process and outcome.