This paper considers the role of network connectivity in supporting context-sensitive applications. A range of context-sensitive applications are analysed with respect to connectivity. Following this analysis a design space is constructed which enables the positioning of context-sensitive applications depending on their reliance on network connectivity and their reliance on local storage. Further consideration of the role of connectivity is achieved through a study of the GUIDE system which has been developed to provide context- sensitive information to visitors to the city of Lancaster. The current GUIDE system utilises a cell-based wireless network infrastructure to provide both location information and dynamic information to mobile GUIDE units. However, coverage throughout the city is not complete and this raises a number of design implications, including how to maintain a visitor's trust in the system when outside of cell coverage.