The single greatest opportunity to improve health and reduce premature death lies in personal behavior. While technology-based behavior intervention has been around for many years, the emerging smartphone and wearable sensing technology brings great promise to push health behavior change further by inferring and predicting real-time behavior occurrence and its context. In this paper, we envision how social and physical context awareness could sustain behavior change motivation and assist health habit formation. We describe our preliminary work that supports this vision and outline the research challenges to be addressed.