There are tens of millions of children and youth in street situations (CYSS) worldwide, the majority of whom are males living in low- and middle-income countries. Many of these children demonstrate impressive adaptability and resilience. The focus of the current research was on the resilience of male CYSS in León, Nicaragua. Qualitative data were collected through individual interviews and focus groups with CYSS, their family members, community members, and staff of a local nonprofit, with the objective of exploring and consolidating local understandings of resilience. Grounded theory analysis of qualitative data yielded a context-specific conceptual model of resilience as it pertains to CYSS in León. Six qualities were identified to represent the experience of resilience in this group: agency, belonging, flexibility, protection, self-regulation, and self-worth. The knowledge generated from this research can serve as a foundation to develop and implement resilience-promoting interventions for CYSS.