Since the 1990s, situations in which culturally significant heritage sites serve as symbolic targets for intentional attacks, leading to the 'destruction of enemy communities,' have frequently occurred. The International Criminal Tribunal for the former Yugoslavia (ICTY), established to prosecute serious violations of international humanitarian law within the former Yugoslav territories, addresses prominent cases of intentional attacks and destruction of cultural property during the armed conflict, specifically targeting the annihilation of ethnic identity. This article examines the implications and limitations of international legal norms regarding the protection of cultural heritage during armed conflicts, focusing on the Dubrovnik Old Town shelling incident, a representative case of cultural property destruction prosecuted by the ICTY. Firstly, the intentional destruction of cultural heritage is undeniably a significant violation of values that the international community must protect. The pursuit of individual criminal responsibility for the destruction of cultural heritage within the international criminal tribunal signifies a substantial advancement in international efforts to protect cultural heritage during armed conflicts. The negative impact of the intentional destruction of cultural property on human dignity and universal human values is undeniable. However, ensuring effective protection of cultural property in the current normative context, where attacks on cultural property for military purposes may be justified, remains challenging. Secondly, military necessity, rooted in customary international law, limits attacks on enemy forces to military objectives, focusing on the centralization of enemy forces, balancing the military necessity of concentrated attacks on enemy forces with humanitarian considerations to protect civilian objects. However, determining what qualifies as a military objective can be challenging, as it depends on the circumstances of combat and operations. Regardless of whether the principle of proportionality is applicable, evaluating the military necessity from the perspective of cultural heritage protection is crucial. ICTY recognizes that even when military necessity justifies attacks on civilian objects, the intentional destruction of cultural heritage can have a significant impact on the psychological well-being of civilians and may upset the balance with military superiority. Thus, careful consideration is necessary when assessing the military necessity in cases where the protection of cultural property, with a higher need for protection than general civilian objects, is involved. Moreover, even if a target has dual-use, being considered a military objective, evaluating proportionality in the attack is essential to prevent harm to civilians, in accordance with the principle of proportionality. In conclusion, the intentional destruction of cultural heritage should be treated as a threat to the common values of the international community, necessitating appropriate legal and policy responses in line with the actual circumstances of the armed coflict. Military commanders should not only view attacks on cultural heritage as inevitable collateral damage but also recognize the gravity of such acts as war crimes and consider them strategically within military operations.