This study explored the impact of parenting satisfaction and shelter comfort on depression and parenting stress among an urban sample of homeless caregivers residing in New York City. This research provides a new understanding of the impact that parenting satisfaction and shelter comfort has on depression and stress on homeless parents ( n = 201). Linear regression results indicated that parenting satisfaction and shelter environment were the biggest influencers of homeless families experiencing more or less parenting stress. Black parents reported significantly lower rates of parenting stress than their non-Black counterparts. Results also indicated that, as parents become more satisfied with their parenting and feel more comfortable at the shelter, they experienced fewer depressive symptoms. We also found that when parents were satisfied with their parenting, they experienced less parenting stress. Study limitations and future research are also discussed.