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Acute stress during pregnancy can have adverse effects on maternal health and increase the risk for postpartum depression and impaired mother-infant bonding. The COVID-19 pandemic represents an acute environmental stressor during which it is possible to explore risk and resilience factors that contribute to postpartum outcomes. To investigate prenatal risk and resilience factors as predictors of postpartum depression and impaired mother-infant bonding, this study recruited a diverse cohort of 833 pregnant women from an urban medical center in Philadelphia, Pennsylvania, and assessed them once during pregnancy in the early phase of the COVID-19 pandemic (April–July 2020) and again at approximately twelve weeks postpartum. Adverse childhood experiences, prenatal depression and anxiety, and COVID-19-related distress predicted a greater likelihood of postpartum depression. Prenatal depression was the only unique predictor of impaired maternal-infant bonding after postpartum depression was controlled for. Women reporting greater emotion regulation, self-reliance, and nonhostile relationships had healthier postpartum outcomes. Policies to increase the number of nonspecialty providers providing perinatal mental health services as well as reimbursement for integrated care and access to mental health screening and care are needed to improve lifelong outcomes for women and their children.