A wall is both a barrier and an opportunity. The ancient walls of Thessaloniki stand as a monument to this. Since their establishment in the 4th century their status and significance in the city has only grown. Thessaloniki was a trading town strategically placed on a hill overlooking the bay below. As it grew, so did the walls with them eventually spanning from the old town down to the bay. The significance of these walls may seem obvious; they protected against military attacks, but this was a rare exception. The true significance of the walls was more related to micro-control; regulating ingress and egress. In its modern context Thessaloniki is no longer a walled city yet walls have and still play a significant role in the spatial development of the city. In this investigation, the dynamic spectrum of spatial outcomes surrounding the city’s boundary conditions are explored revealing the changing cultural dynamics of the city.