In the seemingly vacant and resource rich region known as the Chittagong Hill Tracts, geo-politically crucial in its vicinity to problematic neighbors and populated by communities deemed as threatening to both the identity and the security of the state, an aggressive militarization, development and Bengali settlement agenda has been evolving since 1971. Similarly, a large-scale Israeli civilian settlement project has developed, incrementally, in the occupied Palestinian Territories since the 1967 war under every government since the beginning of Israel’s occupation. Since 1967 there have been upwards of 149 settlements developed in the West Bank alongside a vast network of roadblocks, check points, military bases and physical barriers. This paper explores how states maintain control over contested spaces. In order to tease out what causal factors lead states to resort to a civilian, non-military, settlement policy in contested territories I employ a most-different systems design comparing the well-known case of Israeli settlements in the West Bank to the lesser known case of Bengali settlement in the Chittagong Hill Tracts of Bangladesh. While these cases take place in very different geographic, historical, and cultural contexts, I propose that three causal variables: An exclusionary national identity, a desire for territorial contiguity or defensible borders and internal security, would be sufficient if not necessary for a state to implement an aggressive settlement policy in a contested territory. Contemporary literature on the state has largely abandoned the focus on frontier settlement. Most of the existing studies do not account for the use of non-state civilians to contend with internal security concerns, or as part of a state counterinsurgency strategy in a contested region. This study concludes by arguing that a better understanding of the contested and shifting borders of these two cases, highlighting the factors influencing states to implement settlements and military occupations in contested territories is useful in furthering our current understanding of state repression and territorial expansion, potentially challenging existing scholarly biases as well as furthering our understanding of the root causes of these intractable conflicts.