Over 20 years of scholarship suggests that living in America's poorest and most dangerous communities diminishes the life course development of children and adults. In the 1990s, the dire conditions of some of these neighborhoods, especially those with large public housing developments, prompted significant policy responses. In addition to the demolition and redevelopment of some of the projects, the federal government launched an experiment to help families leave poor neighborhoods through an assisted housing voucher program called Moving to Opportunity (MTO). While families who moved through this program initially relocated to census tracts with poverty rates almost four times lower than their original projects, many returned to communities of moderate to high poverty. Why? We use mixed methods to explore the patterns and the decision-making processes behind moves among MTO families. Focusing on the Baltimore MTO site, we find that traditional theories for residential choice did not fully explain these outcomes. While limited access to public transportation, housing quality problems, and landlords made it hard for families to move to, or stay in, low-poverty neighborhoods, there were also more striking explanations for their residential trajectories. Many families valued the low-poverty neighborhoods they were originally able to access with their vouchers, but when faced with the need to move again, they often sacrificed neighborhood quality for dwelling quality in order to accommodate changing family needs. Having lived in high-poverty neighborhoods most of their lives, they developed a number of coping strategies and beliefs that made them confident they could handle such a consequential trade-off and protect themselves and their children from the dangers of poorer areas.