The nature of contemporary warfare, which is increasingly being waged in urban settings and is often characterised by asymmetry between the parties. Despite a history of ultimately failed urban insurgencies and the significant obstacles that would-be insurgents encounter in cities, worldwide political violence is not only on the rise, but it is also becoming increasingly urban rather than rural. Armed groups, insurgents, terrorists, and criminal gangs are managing violence like never before, from urban riots and endemic urban violence in India and Pakistan to ISIS-sponsored and -inspired shootings, bombings, and vehicular terrorism attacks in Barcelona, Paris, Brussels, Istanbul, and other major European cities, and groups like al-Shabab and Boko Haram carrying out large-scale attacks in Kenya and Nigeria. Nevertheless, the importance of clarifying and/or interpreting the scope of the specific protective regime devoted to medical personnel, facilities and transports. Two particular legal issues deserve examination. The first is whether military medical personnel and objects are to be taken into account in a proportionality assessment under IHL rules on the conduct of hostilities. The second relates to the scope of the notion of “acts harmful to the enemy” that entail a loss of their specific protection, namely their entitlement to be respected and protected.