This chapter aims to present a reflection on some examples of urban security anticipation. Some attempts at anticipation based on urban actors are reviewed, as well as an analysis of their influence on the anticipatory capacity of the city in general. This will allow us to address the central question of the analysis: can a city by itself constitute a security anticipation system? In terms of security, it could be considered that one of the main problems in anticipating the future in cities is the existence of actors claiming both security and insecurity conditions. The discourses, actions, and mechanisms that allow individuals to anticipate a situation of insecurity are confronted with opposing intentions, making anticipation a difficult process. The chapter recovers concepts of anticipation, such as future literacy, identifying their relevance within an anticipatory system. From there, two cases of Mexican cities are taken up, which allow us to review these ideas in terms of security and anticipation. This discussion allows an analysis of the different types of urban actors involved in security, as well as an approach to their anticipation systems. Finally, it concludes with some considerations about security anticipation at the urban level.