The purpose of our research is to evaluate and redesign a position based information system. We report on ethnographic fieldwork about road inspection, i.e. management of large trunk roads. Road inspectors travel to identify defects and disturbances and then handle the problems or delegate the work. The current information system (ProData) allows position-based reporting with the principal purpose of rationalizing paperwork. We argue that the visible interruptions in the work show that the system functionality doesn’t fit with the specifics of their mobile work. Our findings inform the body of research on mobile position based information systems. First, the designers of ProData have focused on the use of position-based information in an organizational setting, whereas the researchers focus on support for individual activities like reminder tools. Mobile work often demands that both these perspectives be addressed. Secondly, we argue that both the researchers and the ProData designers have to pay attention to the practical details of mobile activities and local collaboration. We recommend development of PlaceMemo, a communication system supporting the making and sharing of position based voice messages. This system will support the user in individual as well as collaborative articulation of contingent situations.