The goal of this work is to discuss a shifting paradigm in the execution of armed conflict in regard to the destruction of cultural heritage, and how this change has directly impacted international legal instruments. This work will focus on the modern way in which war is conducted by analyzing the destruction and rehabilitation efforts of the Old Bridge in Mostar and Tombs in Timbuktu. Both of these World Heritage Sites were destroyed during recent internal conflicts and thus demonstrate how the international community and legal instruments are applied. This shift is further emphasized by a final analysis of the current and still developing situation in Syria and Iraq. This work provides evidence in support of a changing model of armed conflict and its relationship with cultural heritage, which poses new challenges, calling into question the validity of previous international legal instruments in regard to the protection of cultural heritage.