Shopping in the real world is becoming an increasingly interactive experience as stores integrate various technologies to support shoppers. Based on an empirical study of supermarket shoppers, the authors designed a mobile context-aware system called the Context-Aware Shopping Trolley (CAST). The purpose of CAST is to support shopping in supermarkets through context-awareness and acquiring user attention, thus, the authors’ interactive trolley guides and directs shoppers in the handling and finding of groceries. An empirical evaluation showed that shoppers using CAST behaved differently than shoppers using a traditional trolley. Specifically, shoppers using CAST exhibited a more uniform pattern of product collection and found products more easily while travelling a shorter distance. As such, the study finds that CAST supported the supermarket shopping activity.