The use of digital technology in school settings is increasing every year, where one aspect of digital technology is robotics in education. In relation to that and of uttermost importance is the issue of how to design teaching and learning activities that includes robot technology in education. In this paper we investigate how open-ended designs can allow children to playfully explore robotics in educational settings, drawing from workshops carried out with three third grade classes of Danish school children, aged 9–10 years old, that interact with robotics in a cross-case study. By the use of video recordings, the unit of analysis focuses on the activities with a special interest on children’s interactions with the robots and with each other. The research questions posed in the study are: (1) What happens when school children use robotics designed for open-ended interactions? And (2) In what ways do children’s playful experiences unfold while engaged with robotics? The study applies a qualitative approach and the theoretical framework used describes open-ended designs as resources to develop playful experiences. In doing so, Vygotsky’s theory on mediation, Hutt’s studies into children’s play with novel objects, and Bird and Edwards’ digital play framework are used as an analytical framework. The results of this study imply that by using an open-ended design in the teaching activity with the robot, which included an exploratory and problem-solving approach, conditions were created for playful and collaborative learning.