The concept of outsourcing information technology (IT) or systems (IS) has been around since mid 1960s. Today, outsourcing has become a potentially viable business solution that many IT managers are looking into in order to remain competitive in the current dynamic business and technological environment. In Singapore, the recent IT outsourcing by DBS Bank has raised the awareness and sparked off the interest to conduct this study. The purpose of this thesis is therefore to investigate this latest IT trend and to look into the concepts and practice of outsourcing in Singapore. An intensive literature review and an empirical survey based on questionnaire technique were conducted to learn about outsourcing concepts and practices. In the literature review, the concepts of outsourcing were explored. The different types of outsourcing practices and trends, categories of outsourcing services, drivers, benefits, risks, challenges and critical success factors of outsourcing based on the lessons learnt from past outsourcing experiences were discussed while the survey assessed the IT/IS outsourcing trend in Singapore. The survey revealed that outsourcing has been a positive experience. Generally, there are differences in views between people of different roles and there is a gap in the understanding and practice of IT/IS outsourcing in Singapore in comparison to the literature.It is learnt in this study that outsourcing is not a perfect and workable solution for everyone. Organizations should always stand back and examine the outsourcing option. The bottom line is outsourcing should always be backed by an objective business case. It should be not a decision that blindly follows the market trend. Organizations should not simply jump into the outsourcing bandwagon without fully comprehending the outsourcing concept. Thorough evaluation of the feasibility of such business venture is necessary.