Sustainable retrofit of existing buildings is becoming increasingly critical in the UAE, aligned with the country’s national sustainability targets and global climate commitments. While international literature widely identifies common barriers—financial limitations, technical challenges, social resistance, educational gaps, and regulatory issues—this research examines how these barriers are experienced within the UAE’s unique context. The study is based on in-depth interviews with 14 senior experts, each possessing over 10 years of professional experience within the UAE. These experts represent a diverse range of sectors, including academia, government, private industry, and non-profit organizations. Their insights reveal several context-specific challenges that influence retrofit adoption in the country. Key barriers identified include the transient nature of the population, lack of benchmarking, difficulty in convincing stakeholders, and the trend of overdesign. Interestingly, unlike findings in studies, limited access to retrofit materials and equipment was not perceived as a major barrier in the UAE. This is part of an ongoing research effort. The next stage will focus on analysing the interrelationships between these barriers to identify the most influential ones and propose applicable solutions for overcoming them. These locally grounded insights aim to support the development of effective, context-responsive retrofit strategies for the UAE’s built environment.