This qualitative study explores homeless young adults’ perceptions of the systemic, situational, and intrapersonal barriers they encounter across multiple systems in trying to exit homelessness and the ways these barriers are interrelated. Thirty-one homeless young adults (ages 18–26) in Phoenix and Tempe, Arizona were recruited for in-depth interviews from two resource centers serving homeless youth. Findings indicate that structural barriers faced by homeless youth include inadequate homeless resources, employment challenges, discrimination by law enforcement, hot climate, lack of transportation, and legal concerns.