The Aegean island of Kalymnos, part of the Dodecanese Archipelago, has long sat at the crossroads of nations and empires. The ruggedness of its terrain belies its prosperity, and, during the regionally destructive transition from Late Antiquity to the Early Middle Ages, Kalymnians distinguish themselves from their neighbors by the construction of fortifications, in contrast to other islanders’ flight and dispersal. Reporting on a preliminary season of site visits and GIS recording, I place Kalymnos within the context of debates on settlement, conflict, and economy in the tumultuous seventh century A.D. From recalibrations of previous GIS calculations to the ‘discovery’ of entirely undocumented ancient settlements, this presentation represents the transition from unwilling armchair archaeology to the long-awaited field-testing of myriad half-blind hypotheses against the truth of the ground, and the knowledge of local experts.