This study examined four categories of self‐reported health and mental health factors and their association with recurrent or chronic homelessness in a sample of homeless Veterans presenting for care for the first time. These factors and their relationship to housing status were examined in a cross‐sectional analysis comparing first‐time or single episode homeless Veterans to chronic or repeat emergency sheltered or unsheltered homeless Veterans. Results revealed that while Veterans with a history of chronic or recurrent homelessness were more likely to self‐report diagnoses of substance abuse problems, any mental health problems, and bipolar disorder, those who were homeless for the first time in their adult life were more likely to report a variety of physical health conditions, economic causes of homelessness, and some other mental health problem. These findings suggest that further work should be undertaken to determine how clinical interventions for Veteran homelessness address different risk profiles and treatment needs based on lifetime homeless history.