“If the homeless programs are working out here, why are people still homeless?” Two years ago, during a winter storm in Portland, I spoke with a man sleeping on the street, freezing under a thin blanket. He wasn’t unaware of services. He knew the programs. He even used some of them. Yet he was still outside. The problem wasn’t a lack of outreach. Outreach workers had contacted him many times. They explained shelters, services, and housing options. None of it changed the outcome. He has now been