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This study broadly examines the relationship between education and democracy. More specifically, its aim is to develop knowledge about the complexity inherent in the school’s democratic mission, with a particular focus on teachers’ didactic considerations concerning pupils’ influence in social studies education in Swedish compulsory school, Years 4–6. The empirical material of this study consists of transcribed interviews in which teachers reflect on when and how student influence can be implemented, what decisions students might be allowed to influence, how and why such influence should be encouraged or limited. The concept of dilemmatic space, as formulated primarily by Bonnie Honig, is employed to analyse the data, enabling the complexity of the teaching profession to be made visible. In addition, two educational–philosophical points of departure have been formulated and subsequently used in the analytical process. The first, “Cultivation and education for democracy”, is inspired by selected texts by Martha Nussbaum, while the second, “Subjectification and education in democracy”, is developed through the work of Gert Biesta. The findings of the study indicate that the teachers’ considerations revolve around aspirations for structural clarity, a sense of security, pupils’ well-being, and what constitutes well-designed teaching arrangements. By conceptualizing these considerations, it becomes possible to make teachers’ complex value-oriented aspirations and positions intelligible. These aspirations are closely linked to what is perceived as valuable to prioritise. The conceptualization of teachers’ value-oriented aspirations helps to illuminate that teachers carry these ideals and aspirations, and that they often must navigate multiple value aspirations simultaneously. Although these value-oriented aspirations are desirable, they give rise to practical dilemmas and tensions. Within these tensions, positions emerge that can be understood as contextually situated judgments in time and space. The tensions require teachers to position themselves in the moment to be able to act. Drawing on the findings of this dissertation, I argue that conceptualising teaching as a dilemmatic space — informed by the school’s democratic mission wherein pupils' influence is integral — can enhance our understanding of the inherent complexity of a democratic education.