Mathematical modelling is as most parts of mathematics education affected by the use of digital technologies. In this chapter, we analyse two modelling cases designed with the aim of supporting students’ development of modelling competency and learning content knowledge whilst explicitly drawing on digital tools. One case addresses the notion of vectors at upper secondary level whereas the other case deals with more advanced uses of differential equations at tertiary level. We employ the notion of media-milieu dialectics from the Anthropological Theory of the Didactic, which allows us to study the role played by the digital tool, the modelling problem and other resources available to the students. Based on this analysis, we discuss to what degree the students demonstrate and develop mathematical modelling competency as well as mathematical digital competency, where we refer to the frameworks emerging from Mathematical Competence Theory. Networking these theoretical frameworks allows us to discuss how the merger between mathematical modelling and digital tools can support students learning of mathematical knowledge.