In the last 15 years, connectivity and communications have increased dramatically. As a matter of fact, from 1990 to 2Q of 2004, the number of mobile phone subscribers has growth from a few million to over 1.5 billion. In the same period, the number of Internet users worldwide raised from 2 million to 810 million (IWS, 2004; Juliussen, 2003). This means that today a large section of the population is dependent on communications and content, and wants to be connected any time and any place, even in their cars (Comunicar, 2002; Microsoft, 2005). To answer this requirement, telematics are being fitted into cars, giving rise to vehicular telematics systems (VTS). Indeed these systems represent the in-vehicle convergence of mobile communications and information processing, allowing drivers and passengers to stay in communication with the world outside their automobile. Vehicular telematics market is projected to be about $17 billion by 2006, equaling a growth by 280% since 2000 (Juliussen, 2003). From a technological point of view, a VTS is composed of three basic components: 1. A two-way wireless communication (voice/data) system; 2. Some location technologies able to identify current geographic position; 3. Some computing technologies, to handle data and manage information flows from/to the user. By fully exploiting the features offered by these systems, exciting new usage scenarios, opportunities, and markets are being available for both end-users and automotive manufacturers. As an example, drivers can receive contextual services, such as updated route calculations, basing on traffic alerts for the selected route, or can perform remote diagnosis of electronic car components, while passengers can access to e-mail and Web sites. In the meantime, new business opportunities are being available for automotive manufacturers, since VTSs allow them to sell “services” and after-market upgrades, to have an open communication channel with buyers during the whole car life-cycle, and to understand their customers’ individual needs, thus providing an exceptional marketing link. This obviously is requiring deep changes in the business model for vehicular original equipment manufacturers (OEM). However, telematics is also affecting their design model, posing challenging technological issues, ranging from embedded real-time aspects, to context-aware ones, to the definition of innovative and safer human-machine interfaces. In this article, we will provide an insight on the new mobile-commerce opportunities offered by telematics, together with the posed technological challenges. In particular, after a brief outline on the evolution of VTSs, we will analyze the services, the business challenges, and the opportunities that next-generation systems will offer. Subsequently, we will describe the technological difficulties posed by VTSs, with particular interest on human-machine interaction (HMI) and the safety issues. Finally, we will depict the future trends on this fascinating scenario.