This paper reports on a comparative study between the structures, regulation and challenges of small and medium size businesses (SMEs) in Australia and two Latin American jurisdictions – Chile and Cuba - with the object of exploring ways in which SME-propitious ecosystem can be configured in an unprecedented crisis situation. It examines the legislation, bodies and regulation in place which deal with SME issues, including consumer protection,and the differing contextual considerations, taking cognizance of the challenges faced during the COVID-19 pandemic. Finally, the paper explores ways in which SMEs can be assisted and advised of their legal rights, including the provision of clinical and advisory support at a university level, and considers the steps taken by governments in mitigating the impact of the COVID-19 pandemic. To compare practices and learn from them the research utilizes three case studies and contrasts the issues faced in an emerging economy such as Cuba with more established frameworks such as Chile and Australia, both OECD countries.