Cities worldwide operate on the frontlines to support forced migrants. Some of these cities even overstep their formal prerogatives by refusing to comply with, and at times overtly subverting, the prescriptions of national authorities. This article builds a conceptual framework to understand such forms of insurgent urban asylum policy-making. We argue that insurgency depends on how city governments mediate the constraints and opportunities that emanate from the horizontal and vertical dimensions of multi-level governance, which capture city-level political dynamics as well as intergovernmental interactions. To illustrate our framework, we compare asylum policy-making in Barcelona, Milan, and Munich during the 2010s “refugee crisis.” While Munich invested in rather uncontroversial integration programs, Milan and Barcelona overstepped their jurisdictional boundaries and supported migrants considered “illegal” by national governments. These insurgent responses were enacted as a “remedy from below,” stemming from a sense of urgency that was not as pressing for Munich’s policy-makers because of the greater capacity of Germany’s asylum system.