Global interest in the field of extended education has increased over the past two decades. Extended education in the context of Swedish school-age educare has a unique position in the school system due to its voluntariness and governance as well as the free time and leisure activities it offers pupils and the lack of set learning outcomes. These features create dilemmas for teachers; thus, this study aims to generate knowledge about the complex and challenging dilemmas of school-age educare teachers in their professional work. The results are derived from a thematic analysis of two sets of data: oral and written reflections from 22 school-age educare teachers. The three themes of the teachers' dilemmas identified concern compulsory school vs. SAEC, offering pupils attractive teaching methods and content, and differing experiences and perspectives among the staff. The dilemmatic spaces that are recognised actualise positions and negotiations in everyday practices in relation to the teachers' professional identities. The findings are expected to be useful as a constructive starting point for policymakers, teacher trainers, and school-age educare teachers to understand this specific educational context and the need for professional development. This study contributes to a further understanding of the multifaceted professional identities of school-age educare teachers.