In May 2017, Tipping Point Community, a Bay Area nonprofit organization, launched a $100 million initiative to halve chronic homelessness in San Francisco in five years. To reach its goal, CHI is relying on three strategies: (1) increasing placements of people experiencing homelessness into permanent housing, (2) preventing people from becoming chronically homeless, and (3) changing systems . This report describes progress made in 2021 toward CHI’s placement goals, successes and challenges, and lessons learned. This report details key progress Tipping Point and city partners made in expanding housing and prevention programming as well as efforts to advance equity and elevate the voices of people with lived experience. The report also looks forward to the last year of the initiative and future evaluation activities.