This study reports the findings of a qualitative study focusing on German first graders’ ability to solve different types of division with remainder problems, before division is formally taught in their classrooms. It is part of a larger research project investigating children’s solutions to division with remainder problems and it focuses on how children reason about these problems depending on the specific context of the task at hand. While there is already evidence that secondary students struggle with a certain type of remainder, little is known about respective abilities of primary students and especially first and second graders. The findings of this study indicate that, while the participating children demonstrated a high level of proficiency in solving division with remainder problems, they encountered significant challenges with the same type of remainder problem that was observed in secondary students. This paper provides qualitative insights into first graders’ thinking and reasoning with respect to their interpretations of the remainder in different context.