This article draws from the knowledge and data collected and documented within a supervision group working with released hostages that were abducted from Israel to Gaza on October 7, 2023. Psychoanalytic thinking provided an incredibly relevant, supportive, and fitting framework for working with the trauma of captivity and its ramifications. Concepts and notions such as setting, life and death drives, internal objects, intergenerational transmission, mirroring, cumulative and persistent trauma, repetition compulsion, and more served as our roadmap through this unfamiliar terrain. These concepts provided an internal anchor upon which we could rely, enabling us to create different forms of meaningful interventions and interpretations, even in the most extraordinary conditions. Nevertheless, these therapeutic encounters with women and children who survived a cruel massacre and 50 days in captivity encountered us with unique dilemmas and significant counter-transference challenges that led to new insights that we will try to share in this paper.