How may users make initial senses around new technology? This question requires an investigation beyond initial sense-making and into ongoing sense-making. An important research agenda is how users may make more senses from ongoing work structuring around technology. The previous studies largely examine how users make initial kinds of sense so as to form certain attitudes towards technology adoption. However, less known to current literature is that users also make ongoing senses as they extensively interact with technology in practice over time. This article presents a qualitative study of the ongoing adoption of CabLink, a Global Positioning System (GPS) which enables vehicle dispatching, implemented by one of the world’s largest taxi fleets, based in Singapore. It analyzes how additional new senses may emerge from a vagary of technology enactments. As a result, users become more sensitive towards adopting technology differentially as they continue to appropriate technology in their work context. This longitudinal research illustrates how local meanings ascribed by different user-groups to a technology may evolve and induce intended as well as unanticipated work transformation. Theoretical and practical implications on ongoing sense-making are discussed.