In January 2013, civic leaders, community stakeholders, and residents came together to release Detroit Future City: 2012 Detroit Strategic Framework Plan, a guiding blueprint for transforming Detroit from its current state of population loss and excessive vacancy into a model for the reinvention of post-industrial American cities. Three years prior, the U.S. Census had reported that the city had lost 24% of its population over the last decade and had experienced a 20% increase in vacant and abandoned property, bringing total vacancy to roughly the size of Manhattan. In addition to physical and economic challenges, Detroiters had also acknowledged significant barriers to effective civic engagement. Foremost among these barriers were a profound sense of immobilization, planning fatigue, and a general perception of cynicism about planning and engagement efforts. These challenges were compounded by historic racial dynamics and tension. This case study elaborates on the comprehensive and innovative civic engagement executed in a citywide planning process called the Detroit Works Project, which took place from late 2010 through late 2012. For the citywide planning process to be successful and sustainable, civic leaders and project funders committed to a planning initiative that would be different from previous efforts, in large part because the “owners” of the process would be diverse and inclusive across all community sectors. The case study, written by three of the key consultants from the project, describes four key civic engagement strategies deployed in the creation of the strategic framework: (1) addressing profound challenges of culture, race, and politics by deliberately building trust; (2) elevating community expertise by fostering a sense of ownership of the process; (3) blending technical and community expertise; and (4) viewing civic engagement as an ongoing two-way conversation rather than a series of large-scale episodic events. This article elaborates on important lessons that other communities might learn from Detroit’s planning initiative in relation to these strategies. It concludes with a brief summary of the results and implications of the civic engagement process.