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Intelligent IT Outsourcing enables practitioners to focus in on the essential issues that need to be addressed so that the fundamental structure of their sourcing strategy and its implementation is sound. The authors provide insight into the challenges likely to be faced and give detailed advice on how to pre-empt and manage these. IT and outsourcing continue to be problematic, not least because fundamental learning about this subject fails to be applied systematically, and because IT is inherently difficult to manage. The economics are not obvious and emerging technologies have to be addressed, therefore IT goes to the heart of many enterprises and interfaces with multiple business units and processes, and there are continuous skills shortages. Unfortunately complexities are not removed in outsourced situations where additional problems come into play, for example the supplier's capabilities, whether the IT is right for an outsourcing solution, and whether the contract is robust but flexible enough to allow for outsourcing to take place. Objectives need to be realistic, and factors such as whether the internal management is mature and capable enough in this field, and the impact of prohibitive switching costs on behaviour once an outsourcing deal has been signed all have to be taken into account. The authors have built up over two decades of research, advisory and practitioner experience that enables them to distil the fundamental challenges in IT and outsourcing and demonstrate how these can be addressed.