Recent years have seen a marked increase in the production and promotion of portable, wireless communication devices: mobile phones with internet access, wireless PDAs such as the Palm VII and smart pagers such as RIM’s 850 and 950. Some claim the presence of such devices in the hands, bags and pockets of so many people heralds a new world of work in which people can be reached and information accessed “anywhere, anytime”. Whether or not access to information in itself can promote new working practices, individuals whose lives revolve around movement between work sites have been singled out as an obvious market for such portable wireless communication devices. Using these devices such “mobile workers” can be in touch with colleagues, collaborators and clients “24/7”, and still sustain non-work social relationships due, apparently, to their constant connectedness whilst mobile. In this chapter we have two goals. The first is to address the design of mobile technologies. This second is to illustrate our design approach, wherein we consider local practices of technology use, but also the broader cultural context in which technologies are designed, produced, bought, sold, used and redesigned. Our ultimate design aim is to build upon existing practices, but also to consider possibilities for the development of innovative technologies that enable new, complementary, practices.