Introduction: Studies are needed to inform the preparation of community nurses to address patient behavioral and social factors contributing to unnecessary readmissions to hospital. This study uses nurses’ input to understand challenges faced during home care, to derive a framework to address the challenges. Methods: Semistructured interviews were conducted to saturation with 16 community nurses in Singapore. Interviews were transcribed verbatim and transcripts independently coded for emergent themes. Themes were interpreted using grounded theory. Results: Seven major themes emerged from 16 interviews: Strained social relationships, complex care decision-making processes within families, communication barriers, patient’s or caregiver neglect of health issues, building and maintaining trust, trial-and-error nature of work, and dealing with uncertainty. Discussion: Community nurses identified uncertainty arising from complexities in social-relational, personal, and organizational factors as a central challenge. Nursing education should focus on navigating and managing uncertainty at the personal, patient, and family levels.