Armed conflict is considered a major risk for cultural heritage since the Second World War and guidelines are prepared by international organizations such as UNESCO and ICCROM on risk management and protection of cultural heritage in conflict-affected areas. However, the main concerns are reducing risks prior to the armed conflict by identifying, analyzing, evaluating, treating and monitoring risks and managing them before the risk occurs. The literature is quite narrow in respect to the ways of protecting cultural heritage and sustaining life for both buildings and people in intentionally destroyed historic settlements. Within this context, this study aims to raise the question on how to manage change in the intentionally destroyed historic settlements and how to strengthen resilience in conflict-affected areas. In order to achieve this aim, an examination on two case studies, Kirkuk Citadel and the Old Town of Van, which were both intentionally destroyed as a result of armed conflict is made using comparative analysis method. The cases are chosen to represent different time periods, scales and types of destruction. Depending on the international law and guidelines, the study tries to understand the impact of armed conflict on the historic settlements embracing tangible and intangible cultural heritage, types of risks that threaten them and the ways to strengthen resilience in such areas. It is revealed as a result of the study that for both case study areas, being in the tentative list of UNESCO World Heritage is seen a primary step to be internationally recognized and to claim help for future actions aiming to reduce risks. Nevertheless, it can be argued that strategies have to be developed depending on the size and level of destruction, and the level of intervention to preserve and to rehabilitate life in such historic settlements, as each intentionally destroyed historic settlement has unique cultural, political and economic characteristics.