In this chapter, we acknowledge the desirability of understanding trends and predicting the future with respect to information technology and its usage, whilst highlighting some existing areas which are particularly interesting in this respect. We predict a wider usage of identity management from an intelligence perspective, using personal transactional information to inform a broader business intelligence, both from an internal organisation perspective and from the broader commercial and marketing perspective. Such intelligence gathering is supported by tools providing functionality such as centralised log management and correlation across disparate information sources, often close to real time. Biometric-related information, such as likeness scores for example, might provide for some interesting systems-related intelligence and we discuss such matters accordingly. We consider both the likely progress and associated issues with respect to virtualisation, including challenges around configuration. Such discussion leads logically to the concept of cloud computing, with which we may experience many challenges, including those around information security and identity management. In this context, we predict a proliferation of cloud identity management services and federated identity models, and posit that the proliferation of cloud technology may lead us into completely new ways of thinking around identity management. Biometrics may have a part to play, although there are some attendant challenges which will need to be carefully considered. We predict that an even greater proliferation of online services and the use of mobile technology will ensue, bringing additional challenges and a new wave of sophisticated cybercrime. We also introduce the TOLL (Total On Line Licensed) model and question factors such as control, ownership, responsibility and data security. We suggest that, hand in hand with TOLL, the concept of professional services will expand and become a major consumed component of many organisations in both the private and public sectors. We additionally consider systems design and the migration towards web services, components and associated architectures as an operational systems model, as well as technology usage from the broader perspective, including ongoing challenges such as complexity, security, ownership, trust and identity theft. The pace of technological change is both exciting and not a little worrying in some respects. This chapter introduces some food for thought in this context and hopefully inspires further discussion.