Clinical dilemmas occur in every practice, yet even experienced and progressive providers well versed in mental health issues for transgender and gender nonconforming people face situations that are especially complex. In this session, four psychotherapists discuss some of their most challenging cases involving trans and gender nonconforming clients, addressing issues such as transference and countertransference, gatekeeping, intersections of identity, social justice, and situations that were diagnostically unclear. These therapists will speak to their clinical impressions, strategies, philosophical concerns, internal struggles, as well as the legal, selfcare, and supervision practices they employed during these clinical relationships. This session is conducted with the objective of helping providers at all levels be more able to address these issues with their clients, and within themselves. For those who attended last year, this presentation will feature new cases.