Combining new educational approaches and educational technologies can make mathematics education more adaptable to pupils’ needs in the 21st century. Our explorative educational study aimed to identify how learning settings and learning environments should be designed to facilitate synthesising flipped approaches to education and using GeoGebra. To discover how to combine flipped approaches and GeoGebra in mathematics education, we conducted a nine-month educational study at a Viennese secondary school. In our study, we focused on pupils’ needs, as pupils are key to combining successfully new educational approaches and using technologies. Analysing our qualitative research data following design-based and grounded theory approaches indicates that the categories (a) clear task definition and task design, (b) feedback, (c) context and benefits, and (d) single-source learning environments are important for pupils when utilising GeoGebra for enhancing flipped education.