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Designing technologies is a process that relies on multiple interactions between design and use contexts. These interactions are essential to the development and establishment of technologies. This article seeks to understand the attempts of healthcare organisations to integrate use contexts into the design of healthcare technologies following insights of the theoretical approaches of social learning and user representations. We present a multiple case study of three healthcare technologies involved in improving elderly care practice. These cases were part of a Dutch quality improvement collaborative program, which urged that development of these technologies was not “just” development, but should occur in close collaboration with other parts of the collaborative program, which were more focused on implementation. These cases illustrate different ways to develop technologies in interaction with use contexts and users. Despite the infrastructure of the collaborative program, interactions were not without problems. We conclude by arguing that interactions between design and use are not naturally occurring phenomena, but must be actively organised in order to create effects.