The language of morality and legality infuses every aspect of the Middle East conflict. From repeated assertions by officials that Israel has “the most moral army in the world” to justifications for specific military tactics and operations by reference to self-defense and proportionality, the public rhetoric is one of legal right and moral obligation. Less often heard are the voices of those on the ground whose daily experience is lived within the legal quagmire portrayed by their leaders in such uncompromising terms. This Article explores the opaque normative boundaries surrounding the actions of a specific group within the Israeli military, soldiers returning from duty in Hebron in the Occupied Palestinian Territories. By examining interviews with these soldiers by an Israeli NGO, it identifies different narratives of legality and illegality which inform their conduct, contrasting their failure to adhere to conventional legal discourses with the broader “legalization” of military activities. Seeking an explanation for this disjunction, it explores the ways in which the soldiers' stories nonetheless reflect attempts to negotiate various normative and legal realities. It places these within the legal landscape of the Occupied Palestinian Territories which has been normatively re-imagined by various forces in Israeli society, from the judicially-endorsed discourse of deterrence manifested in the day-to-day practices of brutality, intimidation and “demonstrating power,” to the growing influence of nationalist-religious interpretations of self-defense and the misuse of post-modernist theory by the military establishment to “smooth out” the moral and legal urban architectures of occupation. The Article concludes by considering the hope for change evident in the very act of soldiers telling ethically-oriented stories about their selves, and in the existence of a movement willing to provide the space for such reflections in an attempt to confront Israeli society with the day-to-day experiences of the soldier in the Occupied Palestinian Territories.