Educators and families frequently use children's picture books to introduce young children to unfamiliar experiences, including the start of school. In this study, we examine 52 U.S. picture books portraying the transition to kindergarten. Specifically, this content analysis explores the depiction of kindergarten teachers, including the demographic characteristics of these teachers, the extent to which these teacher characteristics mirror those of the kindergarteners in their classrooms, the ways teachers interact with kindergarteners, and the learning environments teachers create for entering kindergarteners. Results show that teachers are generally portrayed as abled and female, with White teachers depicted more frequently than teachers from any other racial or ethnic group. Our findings also indicate that many books about starting kindergarten do not depict a mix of racially diverse kindergarteners and teachers or teacher-student racial and ethnic match. Finally, we find that teachers are portrayed in narrow ways; characterized as classroom supervisors who have relatively limited engagement with children and who rarely inspire students in their intellectual pursuits. Overall results indicate a need for an expanded offering of books about starting kindergarten that are more representative of diverse kindergarten experiences, including both more teacher and student diversity as well as images of kindergarten teachers who are actively engaged in children's kindergarten transition.