Studies on software tutoring systems for complex learning have shown that confusion has a beneficial relationship with the learning experience and student engagement (Arguel et al., 2017). Causing confusion can prevent boredom while signs of confusion can serve as a signal of genuine learning and as a predecessor for frustration. There is little to no research on the role of confusion in early childhood education and playful learning, as these studies primarily focus on high school and university students during complex learning tasks. Despite that, the field acknowledges that confusion may be caused by inconsistency between information and a student’s internal model referred to as cognitive disequilibrium known from the theory of cognitive development, which was originally theorized based on observational studies on young children (D’Mello and Graesser, 2012). Therefore, there is reason to expect that the virtues of confusion also apply to young children engaging in learning activities, such as playful learning. To investigate the role of confusion in playful learning, we conducted an observational study, in which the behavior and expressed emotions of young children were collected by familiar pedagogues, using a web app, while they engaged with playful learning games designed for kindergartens. The expressed emotions were analyzed using a likelihood metric to determine the likely transitions between emotions (D’Mello and Graesser, 2012). The preliminary results showed that during short play sessions, children express confusion, frustration, and boredom. Furthermore, the observed emotional transitions were matched with previously established models of affect dynamics during complex learning. We argue that games with a learning objective can benefit by purposely confusing the player and how the player’s confusion may be managed to improve the learning experience.