In this article, the author argues that the Gotlandic hilltop complex, Herrgårdsklint,should be viewed as a fortified hill-site (Sw. befäst höjdbosättning). This phenomenon occured mainly on the East Middle Swedish mainland, where the fortified hill-sites were constructed by the late Early Iron Age period (AD 0–550) élite. The complex comprises a 120 metre long and 2.5 metres high dry-stone wall of limestone built on a large cliff and encloses an area of c. 1.5 ha, in which several significant house foundations of limestone are visible even today. It was once given the antiquarian designation “cliff fort”(Sw. klintborg), a term which has contributed to a rather simplistic approach from scholars. In past archaeological research, Herrgårdsklint, with the rest of the constructions categorized as cliff-forts, has often been seen merely as a “temporary refuge in times of unrest.” This perception has been challenged, however, by a new approach that puts Herrgårdsklint in the spotlight of eastern Gotland during the Roman Iron Age/Migration Period. A recently initiated project, which aims to remedy the weak empirical situation regarding the diverse Gotlandic cliff-forts, has carried out new analyses of the pottery and animal bone material found in a 1940s excavation of a couple of the house foundations. Together with the observation of the architecturally advanced stone wall’s entrance construction (which the author suggests is an imitation of a clavicula-entrance of a sort used by the Imperial Roman army), the results indicate that Herrgårdsklint should be viewed as a strongly fortified permanent/semi-permanent settlement, which controlled a large hinterland that specialized in beef production and shows signs of close connections to Roman ideas.