Information Technology (IT) is a diverse environment and managing all areas of IT has increasingly become difficult for an organization’s internal Information Systems group. Coupled with the fact that performance requirements have become dynamic, there is a greater need to search the world for the most capable supplier(s). An approach towards global outsourcing of software development or offshore development has been witnessed in the United States; however, organizations in Australia have not been as aggressive in pursuing this strategy. This study aims to document the reasons behind this stance via multiple case studies. Specifically, the study aims to document the awareness, practicality, drivers and risks in adopting a pro-active global outsourcing strategy in Australian industry.