This chapter explores the materiality and consequences of technology at the city scale. The authors are looking at city-based systems transformation through a cultural lens. We pose questions about the effectiveness of using culture and the arts as mediators for consentful, place-based technology. In our professional practice, we advise on developing digital capacity, infrastructure, and compelling use cases for technology within the Detroit Cultural Center, an 80+ acre district in Midtown Detroit. Cultural institutions are leading here, unlike the typical practice of allowing technological or governmental entities to organize this work. In this chapter, we discuss how the deployment of technology for festivals, urban screens, technological psychogeography, and mediated oral and visual history are cultural catalysts for developing civic infrastructure in and beyond Detroit, one of the least connected cities in the US.