Which cities become arenas for violent contestation after war? A growing literature has documented how conflict-related violence often continues after the formal end of armed conflict, and also that such violence often is particularly prevalent in urban areas. Such urban unrest cannot simply be understood as a continuation of violence, however: Oftentimes, the cities that see high levels of violence after war were relatively unaffected, or even “safe havens”, during the war. In addition to spatial shifts, the dynamics and actors involved also tend to change in the postwar context. This study seeks to contribute to understanding such patterns. We suggest that a combination of the city’s political importance and the particular characteristics of postwar contestation help explain why some cities are affected by high levels of violence after war. We test this argument using a global sample of postwar cities 1989–2020. We match these cities to data on wartime dynamics, postwar city growth and political context, as well as different forms of violence in the postwar context. We find clear evidence of discontinuity: wartime violence does not predict postwar urban violence. Instead, our results indicate that the likelihood of urban postwar violence is shaped by the city’s political status and the way that the war ended, which condition the intensity and dynamics of continued contestation in the postwar context. In-depth analysis of dynamics of conflict-related violence in five postwar cities (Benghazi, Bujumbura, Colombo, Imphal, and Jaffna) provides additional support for this argument.