We apply the lens of organized system change (Mair & Seelos, 2021) to understand the scaling of efforts to address the complex societal challenge of homelessness. This lens considers how organized efforts problematize and alter aspects of systems understood as complex social realities. To examine historical data on scaling solutions to homelessness in the United States between 1960 and 2021, we deploy an analytical scaffolding that distinguishes between the causal, situation, and problem realms of social systems. By examining the historical evolution of decisions and actions taken across various sectors and system realms, we develop a set of propositions that shed light on the efficacy, legitimacy, and desirability of scaling efforts. These propositions expand current understandings of scaling social innovation anchored in managerial or transactional perspectives. We contribute to the literature on scaling social innovation by integrating historical and system perspectives to comprehend the intended and unintended consequences of organized efforts to address societal challenges and make progress on social problems. Lastly, we evaluate the usefulness of our analytical scaffolding for empirical research on organized efforts to change social systems.