Imagine interconnected objects with embedded artificial intelligence (AI), empowered to sense the environment, see it, hear it, touch it, interact with it, and move. As future networks of intelligent objects come to life, tremendous new challenges arise for security, but also new opportunities, allowing to address current, as well as future, pressing needs. In this paper we put forward a roadmap towards the realization of a new security paradigm that we articulate as intelligent context-aware security. The premise of this roadmap is that sensing and advanced AI will enable context awareness, which in turn can drive intelligent security mechanisms, such as adaptation and automation of security controls. This concept not only provides immediate answers to burning open questions, in particular with respect to non-functional requirements, such as energy or latency constraints, heterogeneity of radio frequency (RF) technologies and long life span of deployed devices, but also, more importantly, offers a viable answer to scalability by allowing such constraints to be met even in massive connectivity regimes. Furthermore, the proposed roadmap has to be designed ethically, by explicitly placing privacy concerns at its core. The path towards this vision and some of the challenges along the way are discussed in this contribution.