Abstract. With the digitisation of society, e-health systems support new contexts that are different from traditional Information Systems contexts, and therefore need to be better understood. In design for complex, new and sensitive contexts, it is not possible to apply known methods and solutions without deeper contextual understanding. The paper intends to answer how the wickedness of the design context when designing digital services for people diagnosed with schizophrenia can be understood -a context that is contradictory and complex, that is, a wicked design context. The paper presents a grounded theory analysis of stakeholder interviews and focus group interviews with people diagnosed with schizophrenia. Four wicked problems are identified: struggle of dependence, contradiction of social interaction, contradiction of trust and counteracting improvement behaviour. The paper also shows the viability of the use of grounded theory for uncovering and describing contextual wickedness.