The purpose of this study was to explore the ways in which cascading disasters (i.e., disruptions to the environment that generate unexpected secondary events of strong impact) shape perceptions of perinatal wellbeing and breastfeeding/formula-feeding practices in south Alabama. Ethnographic research was conducted with perinatal healthcare providers (n = 10) and birth parents (n = 10) in south Alabama during the COVID-19 pandemic and in the aftermath of multiple hurricanes in 2020. Results reveal that concerns related to cascading disasters were exacerbated or eclipsed by system-level challenges that shaped breastfeeding and formula-feeding practices. Specifically, the absence of paid parental leave and community-based breastfeeding support was perceived as profoundly stressful for participants. Birth parents often had to negotiate between breastfeeding/formula-feeding decisions and their own needs. We argue that robust federal and state-level support systems are needed if birth parents and perinatal healthcare providers are to follow guidelines for breastfeeding before, during, and after cascading disasters.