This chapter traces the history of community engagement with an inner urban social housing community over a period of 12 years, drawing on eyewitness auto-ethnography. Through community engaged teaching, learning and research in Glebe, this chapter explores how we connect and collaborate at the local level to build trust and create mutual benefit, impact and positive change. In 2004 the University of Sydney began a tentative engagement in Glebe. The community’s response was cautious, if not hostile. Residents resisted being seen as “research subjects,” seeking instead a more mutual relationship. This chapter explores the terrain of community engagement, understanding this work as one of ongoing relationship negotiation and building. It highlights the importance of trust in transforming the relationship between the University and its local community to mutual learning, action and change. This work fits poorly into new managerial performance frameworks, which hinder the take-up of community engagement by many universities, despite rhetorical statements.