Despite the scale of veteran homelessness and government–community initiatives to end homelessness among veterans, few studies have featured individual veteran accounts of experiencing homelessness. Here we track veterans’ trajectories from military service to homelessness through qualitative, semistructured interviews with 17 post-9/11-era veterans. Our objective was to examine how veterans become homeless—including the role of military and postmilitary experiences—and how they negotiate and attempt to resolve episodes of homelessness. We identify and report results in 5 key thematic areas: transitioning from military service to civilian life, relationships and employment, mental and behavioral health, lifetime poverty and adverse events, and use of veteran-specific services. We found that veterans predominantly see their homelessness as rooted in nonmilitary, situational factors such as unemployment and the breakup of relationships, despite very tangible ties between homelessness and combat sequelae that manifest themselves in clinical diagnoses such as posttraumatic stress disorder. Furthermore, although assistance provided by the U.S. Department of Veterans Affairs (VA) and community-based organizations offer a powerful means for getting veterans rehoused, veterans also recount numerous difficulties in accessing and obtaining VA services and assistance. Based on this, we offer specific recommendations for more systematic and efficient measures to help engage veterans with VA services that can prevent or attenuate their homelessness.