A major distinction of the Syrian revolution lies in the disparate trajectories of protesting in each of its cities. The Capital, for instance, did not witness the spectacular momentum of protests in Hama and Homs during the non-violent phase of 2011. Interestingly enough, this was the same impression that emerged during the earlier upheaval of the 1980s: Hama and Aleppo spearheaded the popular confrontation against the regime and bore the brunt of its violence and destruction. The latter, however, came under the regime control earlier and could not maintain the momentum that the former did. Why did the Hamwis and Aleppines mobilize differently in the first episode of revolutionary confrontation, and what urban traces remained? In pursuit of an answer, this paper seeks to explore the nuanced role of urban planning in the trajectory of mobilization and urban conflict. It acknowledges the critical role of networks and the regime’s institutional arrangement, yet casts the light on how the channels of resistance were informed by the physical reality in each locality. Specifically, the modernist legacy of urbanization in Aleppo, along with broader socio-spatial control, permitted the full occupation of the city, including its Old City and surrounding popular districts. Once compared to the persisting resistance in Hama around the same period, 1980–1982, this observation reveals the fundamental combination of dense networks and urban layout. That is, both Aleppo and Hama harbored dense and conservative communities that challenged the regime, yet differed in their built environment: the Aleppines were torn apart by boulevards that reached to their most rebellious districts, while Hamwis, having maintained their sway over the popular quarters at the center, held their grounds longer. Their endurance culminated in the vicious military onslaught and the 1982 massacre. Challenging mainstream accounts on the period, the analysis will also demonstrate how the spatial history of the earlier round is relevant to the understanding of why the more recent one (2011) did not come to fruition in Aleppo. Relying on a set of urban studies, interviews, and the political memoirs of prominent figures of the opposition, it advances the argument that understanding the regime upgrading of its “terror and enticement” mechanisms by itself does not suffice to explain the political track of these two urban centers and that the socio-spatial and organizational reality of the revolutionaries was germane to their eventual course of action.