This contribution attempts to explore the contradiction between a strategy of exhaustion aiming to establish the conditions for the besieged party to surrender, and the legal and moral imperative of reducing sieges’ adverse impact on civilians. It is structured around two major lines of inquiry. The first examines siege warfare as a military imperative from a historical perspective, looking at its codification in international humanitarian law (IHL) and resurgence in recent history. The second discusses relevant provisions of contemporary law pertaining to the protection of civilians trapped in a besieged area and attempts to lay out some of the challenges of providing humanitarian assistance in such contexts.