The proportionality concept has gained little scholarly attention when it concerns Asymmetric Warfare. Yet its relevance has become imminent during the last Gaza-conflict whereby the Israeli Defense Forces (IDF) were facing an asymmetric adversary. Does the application of the proportionality principle merit a different legal approach in such a context? If so, can a contextual interpretation of said principle have a dual face? And what may be the consequences thereof for the application of superior responsibilities to be imposed on military commanders under International Criminal Law? These are pertinent questions of law which the author seeks to answer in this article.