The historic cores in the Middle East (after this referred to as “ME”) region, a fragmented and thoroughly changed region during the 19th and 20th centuries, have many identities and authenticity challenges. Unfortunately, the rapid development rate, economic and rapid urbanisation, fast population increase, conflicts, lack of appreciation and awareness, and increasing market values gradually replace urban heritage buildings with newer, higher-density identity-less structures. This paper attempts to present the features, obstacles, challenges, and opportunities facing the urban built heritage at the historical cores and the neighbourhood within their physical, cultural and social life in the ME. It analyses questions for maintaining identity and authenticity, the future of traditional physical, technical and functional architectural elements paradigms and their contemporary reinterpretation and rethinking conservation from sustainable technical culture to socio-cultural sustainability. The paper investigates several issues related to the conservation concepts of the urban and architectural heritage in the ME. Special attention is given to the decision-making framework in the conservation practice, the destruction of the traditional urban heritage, and the destruction resulting from the ME region's political changes (modernisation). The focus is to identify, discuss and analyse how to deal with the challenges of maintaining the identity and authenticity of their historic urban cores. Finally, guidelines and framework recommendations are made for possible measures that may be taken for social sustainability.