Medieval Roman frontier management remains understudied, and only rarely have digital humanities methods been applied to it. This article examines a moment in Roman–Fatimid imperial competition in Syria in the early 1030s by using Geographic Information Systems (GIS) analysis. The Syrian Coastal Mountains south of Antioch were the location of a failed Roman attempt to establish Naṣr ibn Musharraf as a client. As relations broke down, he sought Fatimid support. The brief ensuing conflict is revelatory of long-term patterns in frontier management, while spatial analysis within a GIS framework provides insight into the role of geomorphology in how these events unfolded.