European users have eagerly adopted novel forms of digital media and related information and communications technologies (Stanton, 2001), making them a part of their increasingly varied and segmented cultures (Brown, Green, & Harper, 2001). For example, the young are active consumers of music, videos, movies, and games; businessmen on the other hand need more and more working tools and applications that enable connectivity when they are on the move. A not very dissimilar scenario is envisaged on troops in action where work on tactical and strategic information and mission management, command, and control, including real-time mission replanning, are essential. All these users rely on the Internet, i-TV, and mobile phones, and they have adapted all of these into the fabric of their lifestyles, or in short, their mobile life. But, functionality cannot be the main driver for design as mobile life is also deeply founded upon shared values and worldviews of the users, pleasure, enjoyment, culture, safety, trust, desire, and so forth (Rheingold, 1993). For example, WAP (wireless application protocol) technologies seemed to provide a powerful tool to the mobile worker. However, it is well known the fraud of WAP mainly due to the scarce usability, high usage cost, and inadequate range of the services provided together with intrinsic limitations of the device itself (insufficient memory storage, low battery autonomy, poor screen resolution, etc. [Cereijo Roibás, 2001]). However, some WAP applications have been widely used by Italian users. The success of this system of applications is due to its efficiency, effectiveness, and relevance for some specific work purposes. Each of the services will be analysed, describing the expected use of each service and the actual use of it by Italian users.