This essay explores the dynamics of literature and reading within the Swedish educational context, focusing on teachers' perspective on student self-selected literature and how self-selected literature can be included in the school curriculum. The two key questions are “What opportunities and challenges do teachers identify when working with student-selected fiction literature?” and “What role do librarians play in encouraging reading among the students?” Through survey responses from teachers, the pros and cons of working with student selected literature are discussed. Subsequently, interviews with school librarians follow to deepen the understanding of the role of school libraries. The study uses the sociocultural perspective, which means considering how learning is tied to the situation and how students are influenced by their social surrounding. Major findings highlights that the free choice serves as motivation and ignites engagement, but it is not without its challenges. Both educators and librarians emphasize the importance of cultivating habits related to library navigation and literature selection. The study underscores the essential role of librarians alongside teachers in guiding students through the world of literature. Additionally, it explores factors influencing literature teaching such as the tension between canonized literature and youth literature, access to literature, the challenge of selecting appropriately leveled text and the need to ensure students are engaging with their book of choice.