In this position paper we present an on-going case study where the aim is to design and implement mobile technologies for self-care for patients with type 2 diabetes. The main issue we are addressing in this paper is how to bridge clinical and non-clinical settings when designing self-care technologies. Usability, User Experience and Participatory Design are central aspects of our research approach. For designing with and for patients in home settings and everyday life situations, this approach has so far not been problematic. However, when it comes to designing with and for user groups located within a large healthcare organization, in a highly institutionalized clinical setting, the situation is different. We have recently introduced the Health Usability Maturity Model (UMM) to our project partners as a potential tool for bringing usability and participa-tory design issues to the fore as strategic assets for transforming healthcare delivery with ICT.