This article reconstructs how Arab doctors, medical missionaries, British counterinsurgents, and Palestinian rebels negotiated and contested the legitimate role of medical workers and healthcare in times of colonial conflict. Drawing insight from a medical anthropological literature which challenges the notion of medical neutrality as normative, and setting mandate Palestine alongside other case studies of medicine in times of conflict from the interwar Middle East and North Africa, this article argues that while healthcare and medical authority could be put to work to support the colonial status quo, they could serve other, more radical ends too. To highlight the complexity of the political positioning of medical workers and healthcare, this article focuses on the town of Hebron during the great revolt which rocked the foundations of British rule in Palestine between 1936 and 1939, and relies on a range of colonial and missionary archival sources. The first part of the article uses the case study of an Egyptian medical doctor who took up political office in the town in moments of crisis to show how medical authority could be consciously transmuted into a force to uphold a besieged political order. The second part draws on the diary of a British mission doctor to reconstruct his efforts to assert medical neutrality during the great revolt, and—more strikingly still—how Palestinian insurgents participated actively in this attempt to transplant international legal protections to Hebron. The final part traces the incorporation of healthcare into the strategies of both British counterinsurgents and Palestinian rebels, with the British policy of collective punishment indirectly but appreciably degrading access to healthcare for Palestinians, and Palestinian counterstate ambitions extending to the establishment of insurgent medical services in the hills.