To advance large-scale efforts to end veteran homelessness, an understanding of factors that contribute to housing insecurity is necessary. Common risk behaviors (e.g., substance use and risky sexual practices) are associated with lengthier experiences of homelessness among the general homeless population, but less understood among homeless veterans. Additionally, whether emerging risk behaviors among veterans (e.g., sensation seeking and aggression) are associated with lengthy homeless experiences is unknown. Data were drawn from a sample of Los Angeles County veterans surveyed using a mixed nonprobability sampling strategy, which included recruiting veterans via national and local veterans service organizations, college organizations, and social media campaigns. Measures aligning with factors of sensation seeking (reckless driving, gambling, suicidal ideation); substance use (alcohol misuse, tobacco use, driving while intoxicated); risky sexual practices (risking getting a sexually transmitted disease); and aggression (looking to start a fight) were tested in multivariate, multinomial logistic regression analyses to determine their association with varying lengths of homelessness in the past year (less than 1 month, 2-6 months, 6 months to 1 year). Risking getting a sexually transmitted disease, gambling, suicidal ideation, alcohol misuse, tobacco use, driving while intoxicated, and looking to start a fight were associated with 6 or more months of homelessness. Several indicators of risk were associated with brief periods of homelessness, including gambling and looking to start a fight. Although a clear exposure-response effect was not detected with risk behaviors, results suggested there may be some wavering of engagement in risk behaviors over time. Findings suggest sensation seeking and aggression risk behaviors should be included in risk assessments and prevention efforts along with substance use and risky sexual practices to reduce veterans' risk of becoming homeless and reducing risk of chronic homelessness. Further research is needed to understand the trajectory of these risk behaviors and the mechanisms that underlie the association between these risk behaviors and homelessness for veterans.