Although island disputes have returned to the geopolitical theatre on a small scale, to date, virtually no previous research on territorial interstate island disputes and violent escalation exists. This paper argues that when an island is positioned in a strategic location, because of its unique attacking, defending, and trade capabilities this may induce a willingness towards- and eventual use of violence in the attempt to conquer or defend the territory. This paper attempts to answer: under what circumstances do island disputes escalate? by modelling the influence of strategic locations on violent island disputes. It draws observations from Altman (2020c) and a novel data frame (1920 – 2020) with additional cases and an alternative operationalization of strategic locations along important lines of communication. It finds that island disputes are more likely to occur without BRD than non-island disputes. Meanwhile, island disputes escalate violently more often than they do not. An island’s strategic location, notwithstanding a broad or narrow operationalization, does not have a statistically significant effect on a violent outcome of a dispute. Instead, the presence of military garrisons, ceteris paribus, resulted in the most statistically significant effect. Consequentially, the causal mechanisms were adapted to include military garrisons.