Background: Infants with medical complexity are increasingly cared for at home, creating unique challenges for their caregivers. The sickest of these are those with chronic critical illness (CCI). These infants’ medical fragility and resource‐intensive needs puts them at increased risk for suboptimal transitions from hospital‐ to home‐based care. It is unclear whether, and if so, to what extent clinicians gather and use knowledge of a family's home context during discharge planning. Methods: This study is a pilot of a novel program, using Photovoice methodology, which aims to record and reflect the experience of caring for a child with CCI at home from caregivers’ perspectives and to provide direct feedback to inpatient discharging clinicians, with the goal of increasing awareness of (a) the importance of home context and (b) current discharge limitations. Results: Through photographs, parents described the importance of developing new routines, learning how to be a family, the impact of medical technology on nearly all aspects of everyday life, the critical role played by clinicians during the transition home, and feelings of social stigma and isolation. Clinicians, in turn, learned about gaps in discharge planning and the value of making families part of the decision‐making team. They also found meaning in seeing the children they had cared for doing well at home, which subsequently bolstered enthusiasm for their job. Conclusions: Findings from this pilot study highlight the importance of understanding the lived experience of families caring for medically complex children at home and suggest that this knowledge can be used to address gaps in the transition home.