In asymmetric conflicts the lines of distinction between protected civilians and combatants as well as military and civilian objects are often blurred. Hostilities are frequently shifted into the proximity of urban and civilian surroundings and fighters deliberately mingle with the civilian population. As a result the risks for the civilian population but also for soldiers operating on the ground are significantly increased. In this constellation, compliance with the humanitarian rules regarding the conduct of hostilities, in particular the principle of proportionality and the obligation to take precautions prior to an attack, is of utmost importance. At the same time, asymmetric conflict structures bring to the fore a number of questions pertaining to the concrete application of the humanitarian rules regarding the conduct of hostilities. Pursuing these particular questions is the objective of this contribution.