School leadership is found important for school development and student learning. Consequently, the interest in professional leadership education for principals has increased. In Sweden, professional leadership education for novice principals was made mandatory in 2010. Moreover, enhanced focus on leadership for teaching and learning in terms of 'pedagogical leadership' is highly topical. This study aims to deepen our knowledge of novice principals' experiences of pedagogical leadership practices and relate these to their paths toward principalship. The study follows a qualitative and situated design and adopts a practice-based approach. Observations were conducted in the educational and workplace practices of novice principals in Sweden and interviews were conducted with principals and teachers. Using a conceptual framework of Wenger (1998), the analyses show that principals experience challenges concerning pedagogical leadership if their competence and experience are not aligned with practice and context. This mismatch seems to impair their pedagogical leadership practice. In addition, a lack of leadership experience obstructs their learning in the professional leadership education for principals.