Law school clinics frequently collaborate with outside organizations. Traditionally, these collaborations are with others who share similar goals and priorities – community organizations, non-profits, or other legal services organizations. However, the complexities of legal practice often require lawyers – and therefore clinics – to collaborate with traditional adversaries for the sake of their clients or an issue at large. As clinical faculty in post-conviction defense clinics, we frequently enter into collaborative relationships with prosecutors and law enforcement. This collaboration includes working with formal Conviction Integrity Units, informal relationships with law enforcement regarding access to evidence, or working with prosecutors on consent resentencing or Second Look cases. The results of these collaborations vary significantly. Trust is built and trust is broken. Sometimes the relationships break down. But these relationships forged between traditional adversaries are a necessary and often fruitful aspect of our work. Uncomfortable collaborations expose our students to unique aspects of lawyering. Regardless of the outcome, students gain critical lawyering skills, including how to approach and work with an adversary toward a common goal, communication and negotiation skills, nuanced client counseling, and coalition building. Students learn to evaluate and navigate difficult relationships from a client-centered perspective, including when to move forward and when to walk away. These relationships may be particularly challenging for us as clinicians, who have often spent years working in opposition to those with whom we are now working alongside. This session will explore the unique pedagogical opportunities and challenges that these collaborations present. We will explore topics including: building trust between traditional adversaries, advising clients about potential benefits and pitfalls of the collaboration, navigating complex ethical issues that may emerge, how to move forward if and when the collaboration breaks down, and how to keep working within the collaboration in other cases if necessary.