Profile-driven personalization based on socio-demographics is currently regarded as the most convenient base for successful personalized advertising. However, signs point to the dormant power of context recognition: Advertising systems that can adapt to the situational context of a consumer will rapidly gain importance. While technologies that can sense the environment are increasingly advanced, questions such as what to sense and how to adapt to a consumer’s context are largely unanswered. In this chapter, we analyze the purchase context of a retail outlet and conceptualize it such that adaptive pervasive advertising applications really deliver on their potential: showing the right message at the right time to the right recipient.