The Invest Health initiative, led by Reinvestment Fund with support from the Robert Wood Johnson Foundation, has worked with 50 small and mid-size cities across the United States since 2016 in developing strategies to align investment capital with other resources and policies to address the social determinants of health in community development. A critically important element of health and equity-focused community development, and a program principle of Invest Health, is authentic community engagement. This case study highlights the strategies, challenges, and lessons learned from community engagement efforts in five Invest Health cities: Hartford, CT; Lansing, MI; Missoula, MT; Roseville, CA; and Spokane, WA.