In Mexico and Latin America, schools are confronted by a complex context, marked by high levels of violence that shape the life of schools. This situation is coupled with policies of “convivencia” oriented to prevent, address, and eliminate school violence that are often contradicting and punitive. In dialogue with previous research, this chapter reflects on the changes in moral concerns after two decades and following the declaration of “War on Drugs.” The authors have conducted qualitative research among elementary school principals in Guanajuato, Mexico, where they ask: have the moral conflicts of Mexican principals been transformed in contexts infiltrated by violence? How do they confront coexistence policies that impose labor sanctions for them or their teachers’ failures or omissions? What perspectives for action emerge? Paradoxically, the rise of violence appears to have fostered a greater concern on student wellbeing and transformed principal’s and teacher’s reflections, while at the same time educational policy has enhanced their own feelings of vulnerability.