This chapter investigates issues related to the global transition of an enterprise through the application of information technology and information systems. It starts with the discussion of the issues that are critical to the successful transition of an enterprise to transborder business operations using information systems. The expected outcome of such transition would be a globalized organization that would not be limited by geographical and time zone barriers, nor restricted by cultural differences. The global transition issues are further classified into five categories embracing business information systems management, information technology management, people management, end user management, and culture. It is then followed by a comprehensive examination of individual issues that is vital in understanding their impact on the transition and how to alleviate that impact. The chapter concludes by indicating a future research direction that might augment the development of this emerging field.