This paper demonstrated that IT outsourcing is not as simple as 20 years ago. Experiences gathered over the past two decades has revealed that outsourcing entails varied complexities which can be best managed when evaluated from distinct perspectives. The age of IT offshoring 2.0 is coming. In the IT offshore 2.0, cost reduction is no longer the only reason for business to enter. Beside the cost reduction, the value creation will play a key factor in the future IT offshoring.