Alcohol and drug use are commonly associated with the experience of homelessness. In order to better understand this, we explored the prevalence of drug and alcohol use as it related to successful re-housing within a sample of first-time single homeless adults at municipal shelters. From within this sample, we compared the features of recurrent homelessness with those of chronic homelessness and of being stably housed. We interviewed 344 subjects upon shelter entry and followed each one every six months for 18 months using standardized social and mental health measures. We analyzed baseline assessments relative to housing experiences during follow-up using Chi square and multinomial logistic regression. Eighty-one percent (N = 278) obtained housing over 18 months, of which 23.7 % (N = 66) experienced homelessness again. Recurrent homelessness was more common among those with a high school education and if initially re-housed with family. Bivariate analysis resulted in the observation of the highest rate of alcohol and other drug use among this recurrent group and multinomial logistic regression supported this only with the coupling of arrest history and diagnosed antisocial personality disorder. With relatively high rates of recurrent homelessness, there were differences between subjects who experienced recurrent homelessness compared to those who were stably housed and with chronic homelessness. That alcohol and other substance use disorders were associated with recurrent homelessness only if they were linked to other risk factors highlights the complexity of causes for homelessness and a resultant need to organize them into constellations of causal risk factors. Consistent with this, there should be initiatives that span bureaucratic boundaries so as to flexibly meet multiple complex service needs, thus improving outcomes concerning episodes of recurrent homelessness.