Traditionally, the military is associated with obedience, rule compliance and limited discretion on the part of its personnel. This contribution shows that this imagery has been superseded and argues that changes in mission outlook and the partial shift towards police-like work necessitates a revaluation of military discretionary autonomy. In addition, it explores the moral implications of this constabularization of the military and discusses how the moral demands police officers face as street-level bureaucrats might apply to military settings. By comparing the military profession with police officers’ discretion and the moral character of their work, this chapter aims to provide a particular perspective on what it might mean to be a contemporary soldier.