This study examined the relationship between family communication, school engagement, negative peer behaviours, and depressive symptoms in a sample of youths experiencing homelessness. Interviews were conducted with 123 youths experiencing homelessness. Outcome measures included youth self-reports of negative peer behaviours, family communication levels, school engagement, and depressive symptoms. After controlling for demographic variables, higher family communication (b = -0.38, t = -2.74, p = 0.007) and higher school engagement (b = -4.32, t = -2.61, p = 0.01) were significantly associated with lower levels of depressive symptoms. Negative peer behaviours were not associated with depressive symptoms in the sample. Family communication and school engagement may serve as protective factors against depressive symptoms in youths experiencing homelessness. Practitioners who work with youths experiencing homelessness may collaborate with the youths, schools, and families to improve school engagement and family communication when possible.