The digitalisation of school systems and teaching often comes with expectations to enhance both equity and student outcomes, particularly as stated in policy documents. When curricular goals relating to student’s proficiency in using digital tools in their daily lives are introduced, teachers bear the responsibility of ensuring that these goals can be achieved by all students. This article analyses teachers’ perspectives on the interplay between digitalisation, digital competence, equity, and students’ increased attainment of curricular goals. The interviewed teachers worked from preschool to upper-secondary school levels in the same municipality in Sweden, and their responses were subjected to a thematic analysis. The analysis shed light on three dilemmatic spaces, namely flexibility in teaching and learning, equity and students’ increased goal attainment, and becoming a citizen. Within these dilemmatic spaces, teachers faced the challenge of making decisions regarding their actions and their alignment with various expectations, including the well-being of their students, institutional rules and regulations, and policy guidelines.