Design methods are increasingly used in the healthcare context. However, there is a clash between the playful culture of design and the professional culture of healthcare. Amid this culture clash is an opportunity to critically reflect on the benefits and risks of playfulness within critical contexts. This paper investigates the tensions that emerge by unpacking examples of playful design explorations within health and care systems in Sweden and Norway. In doing so, we offer reflections on the implications of using playful explorations as an extended form of caring within such systems.