The resilience and capacity of historic buildings to adapt plays a vital role in mitigating climate change through adaptive reuse. The adaptive reuse of buildings is a practical substitute to demolition and has substantial economic, environmental and social benefits. However, tensions exist between the retention of heritage buildings and conformance with regulatory requirements (e.g. energy efficiency to reduce greenhouse gas emissions, disability access, etc.). This raises questions about whether regulatory systems can embrace both green building technologies and heritage conservation principles. This paper examines the challenges/barriers to successful adaptive reuse projects in Australia using a qualitative approach that involves multiple case studies and in-depth interviews with industry experts coupled with field observation and building plan appraisals. The findings show that compliance to codes/regulations and current design requirements are the major challenges encountered in undertaking adaptive reuse projects. The underlying parameters of the identified challenges will serve as an initiative for formulating prospective regulations that address changing building use, encourage the integration of modern technologies and inhibit unnecessary building demolition for future global climate protection.