Nowadays, digital tools for mathematics education are sophisticated and widely available. These tools offer important opportunities, but also come with constraints. Some tools are hard to tailor by teachers, educational designers and researchers; their functionality has to be taken for granted. Other tools offer many possible educational applications, which require didactical choices. In both cases, one may experience a tension between a teacher’s didactical goals and the tool’s affordances. From the perspective of Realistic Mathematics Education (RME), this challenge concerns both guided reinvention and didactical phenomenology. In this chapter, this dialectic relationship will be addressed through the description of two particular cases of using digital tools in Dutch mathematics education: the introduction of the graphing calculator (GC), and the evolution of the online Digital Mathematics Environment (DME). From these two case descriptions, my conclusion is that students need to develop new techniques for using digital tools; techniques that interact with conceptual understanding. For teachers, it is important to be able to tailor the digital tool to their didactical intentions. From the perspective of RME, I conclude that its match with using digital technology is not self-evident. Guided reinvention may be challenged by the rigid character of the tools, and the phenomena that form the point of departure of the learning of mathematics may change in a technology-rich classroom.