This study examines social estrangement factors associated with 3 forms of income generation used by homeless young adults: formal sources (i.e., full-time, part-time, temporary employment), informal sources (e.g., selling personal possessions, selling drugs, theft, prostitution), and the combination of formal and informal sources. A sample of 601 homeless young adults was recruited from 3 cities (Los Angeles, CA [n = 200], Austin, TX [n = 200], and Denver, CO [n = 201]) to participate in semi-structured interviews. A multinomial logistic regression model is used to assess whether demographic, homelessness history, arrest history, transience, peer substance use, antisocial personality disorder, and substance use disorder variables predict involvement in the 3 forms of income generation as compared with participants who report no work-related income. Homeless young adults who earn income through formal sources are differentiated from those who report no work-related income by 2 variables: gender and primary residence. Those who earn income via informal sources are differentiated from homeless young adults who report no work-related income by 6 variables: age, city, primary residence, transience, peer substance use, and antisocial personality disorder. Participants who earn income through a combination of formal and informal sources are distinguished from those who report no work-related income by 7 variables: gender, city, primary residence, transience, peer substance use, antisocial personality disorder, and substance use disorder. Study findings suggest there might be value in combining supportive housing, employment, and clinical services for this population.