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. Tipping Point’s Chronic Homelessness Initiative(CHI) is the largest private investment to address homelessness in the city’s history. 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 that feed chronic homelessness and with which people experiencing chronic homelessness frequently interact. This brief provides a snapshot of the progress made in 2020 toward CHI’s placement goals and successes, as well as the challenges the initiative experienced. The brief also looks forward to what needs to be done to meet the goal in two years.