In many countries, such as Switzerland, political demands on kindergartens are increasingly focused on the early acquisition of academic knowledge. However, pretend play and the development of imagination should be priority objectives for preschoolers. The challenge, then, is to propose working methods adapted to these early stages of schooling that no longer oppose play and learning in preschool. This chapter proposes to document classroom practices that foster a dialectical articulation between play and curriculum knowledge, between learning in preschool and preparation for school. The situations presented here show how it is possible to link the specificities of preschool learning, particularly imaginary play, and the development of imagination, with the development of children’s interest in disciplinary learning.