Violent conflicts involving non-State armed groups challenge conventional perceptions of war and armed conflict. Criminal enterprises (transnational organized criminal groups including gangs and cartels) are involved in violent competition for both profit and territorial control in many parts of the world. This paper examines the situation in Mexico and Brazil as case studies to assess the legal challenges to criminal armed violence when criminal groups battle among themselves and the State. The paper focuses on the operational challenges and considerations facing police, military, and security forces and justice institutions to illuminate the legal challenges.