Introduction: Unsheltered homelessness is a strongly debated public issue. The study objective is to identify personal and community characteristics associated with unsheltered homelessness in veterans and to test for interactions between these characteristics. Methods: In a 2018 national survey of U.S. veterans with homeless experiences; investigators assessed unsheltered time; psychosocial characteristics; and community measures of shelter access, weather, and rental affordability. Associations between these characteristics and unsheltered status were tested in July–August 2020. This study also tested whether the count of personal risk factors interacted with community characteristics in predicting unsheltered status. Results: Among 5,406 veterans, 481 (8.9%) reported ≥7 nights unsheltered over 6 months. This group was more likely to report criminal justice history, poor social support, medical and drug problems, financial hardship, and being unmarried. Their communities had poorer shelter access and warmer temperatures. The likelihood of unsheltered experience rose with risk factor count from 2.0% (0–1) to 8.4% (2–3) and to 24.2% (4–11). Interaction tests showed that the increase was greater for communities with warmer weather and higher rents (p<0.05). Conclusions: Among veterans experiencing homelessness, unsheltered experiences correlate with individual and community risk factors. Communities wishing to address unsheltered homelessness will need to consider action at both levels.