Health care systems struggle to consistently deliver integrated high-quality, safe,and patient-centered care to all in an economically sustainable manner. Inequity of access to healthcare services and variation in diagnostic and treatment outcomes are common. Further, as healthcare systems become ever more complex, iatrogenesis and counter productivity have emerged as realdangers. In exploring this paradox, this paper considers a subset of those in society living with chronicconditions. Their attributes and circumstances have led to them being marginalized or excludedfrom ‘end-user’ engagement and/or from their requirements being incorporated into technologysupported chronic disease management initiatives. Signiﬁcantly, these citizens are often the mostvulnerable and socially disadvantaged and tend to achieve poorer results and cost more per capitathan the ‘average patient’ in their interactions with the health care system. Critically, this paperargues that a truly people-centered technology supported chronic care system can only be designedby understanding and responding to the needs, attributes and capabilities of the most vulnerable insociety. This paper suggests innovative ways of supporting interactions with these ‘end-users’ andhighlights how reﬂection on these approaches can contribute to emancipating the health system tomove towards more socially inclusive eHealth solutions.