Research has shown links between homelessness and criminal legal involvement in military veterans. The present study aimed to determine the magnitude and directionality of this association by investigating the incidence of, and factors associated with, homelessness preceding criminal arrest among veterans. Data on incarcerated veterans (N = 1,602) were analyzed from the 2016 Survey of Prison Inmates conducted by the U.S. Bureau of Justice Statistics. In this survey, 27% of incarcerated veterans reported homelessness 12 months before criminal arrest. In multivariable logistic regression analyses, higher odds of experiencing homelessness preceding criminal arrest were associated with younger age, non-White race, substance use disorder (with or without serious mental illness [SMI]), history of previous arrests, parental history of incarceration, and history of homelessness before age 18. These factors were found to be the same for nonveterans, as were rates of homelessness before arrest. However, incarcerated veterans were more likely to have mental disorders, including SMI, posttraumatic stress disorder (PTSD), and personality disorders. In contrast, incarcerated nonveterans were more likely to have a criminal history, including past arrests, parental incarceration, and juvenile detention. Although policymakers may be aware that some veterans they serve are at risk of criminal legal involvement, these national data reveal the magnitude and directionality of this problem: more than one in four incarcerated veterans experienced homelessness before criminal arrest. Identifying characteristics of veterans who experienced homelessness before criminal arrest directly informs service providers of demographic, historical, and clinical factors to evaluate and address to prevent criminal legal involvement. (PsycInfo Database Record (c) 2023 APA, all rights reserved).