Globalization processes are continuously pressuring cities and regions to connect, learn, reject or adapt. This chapter examines the role of information and communication technology (ICTs) in this respect. One of the most important features of network technology, especially the Internet, is the potential to connect, thereby enabling individuals, groups and organizations to overcome numerous organizational, functional and territorial boundaries and barriers (Bekkers and Homburg 2005). The World Wide Web is claimed to play a key role, even reinforcing globalization (Castells 1996/2000, 2004). To what extent and in what way do ICTs bring advantages to city and regional politicians in the performance of their functions as councillors? Do such advantages also bring a competitive edge to regions as development agents and an enhancement of their qualities as democratic institutions?