Members of the CoPro 2.0 cohort, a $2.6 million grantmaking initiative launched by The Kresge Foundation in 2021 to support the next generation of free college programs, gathered at Foothill College in Los Altos Hills, California, to develop strategies that would contribute to the expansion and sustainability of the movement. Throughout the convening, the grantees were challenged to identify common trends, successes, and challenges across their focus areas of program innovation and redesign; research on financial sustainability; and strategic local implementation. The identified challenges and strategies moving forward are outlined in this policy brief.