We used Design Probes (DP) as a communication tool supporting designers to learn about users, collecting selfdocumentation data from children and parents about their everyday chronic disease management. DP are also applied as alternative strategies to perform ethnographic study in a domestic environment and to elicit inspirational data for the design of an educational interactive eBook for newly diagnosed children with type 1 diabetes mellitus (T1DM). Eight probe activities were designed for children between the ages of 812 years who have diabetes and their caregivers, which were then distributed to seven families. The main issue discussed in this paper is the adaptation of the DP to the users (children and parents) and the results produced by participants who used them.