Families experiencing homelessness face a number of risks to their psychosocial health and well‐being, yet few studies have examined the topic of parenting among homeless families. The purpose of this multimethod, descriptive study was to acquire a better understanding of the psychosocial status and life experiences of homeless parents residing in transitional housing. Quantitative data were collected from 69 parents and primary caregivers living in a transitional housing community, with a cohort of 24 participants also contributing qualitative data. The quantitative results suggest risk associated with depression, parenting stress, and negative parenting practices. The qualitative findings highlight five themes that convey both the challenges faced by homeless parents as well as the resilience they display in spite of such adversity. These results extend current scholarship on homeless families with children and can better inform how couple and family therapists work with this at‐risk population.