In this chapter we propose a decision support system for privacy management of context-aware technologies, which requires the alignment of four dimensions: business, regulation, technology, and user behavior. We have developed a middleware model able to achieve compliance with privacy policies within a dynamic and context-aware risk management situation. We illustrate our model in more details by means of a small prototype that we developed, and we present the current outcomes of its implementation to derive some pointers for the direction of future investigation.