Children Living with Health Complexity (CLHC), whose multiple, severe and chronic conditions differentiate them from those with “complicated” conditions, rely life-long on a vast and ever-shifting array of care providers. Their parent caregivers face a fragmented health care system, disconnected medical records, inter-stakeholder communication barriers and an impenetrable accumulation of documentation – from mundane to life-critical, and largely on paper. They must coordinate care while organizing, tracking and transmitting trends in many health parameters to myriad care providers. We engaged with parent caregivers of CLHC from 12 families through an iterative, 3-phase co-design process to understand their needs for a future digital management system. We share our deepened understanding of their information-centered challenges, a set of principles for how design best-practices need to shift when targeting this acutely high-needs group, and a medium-fidelity prototype user interface which from the ground-up prioritizes caregiver-centered data integration and humanization of the child and family, as well as integrated health record access.