What is the role of shared calendars for home health management? Utilizing a maximum variation sampling method, we interviewed 20 adult individuals with diabetes and 20 mothers of children with asthma to understand calendar use in the context of chronic disease home health management. In comparing the experiences of these two groups, we explore participants' use of tools for organizing tasks and appointments, their strategies for capturing health and non-health events in the family calendar system, the ecology of artifacts that intersect with their scheduling tools, and the failures they experienced while managing their calendar systems. Through this work, we offer a context-specific perspective of schedule management strategies for individuals and families who must integrate their handling of chronic illnesses with everyday living.