The significant development and use of digital technologies has opened up diverse routes for learners to construct and comprehend mathematical knowledge and to solve problems. This implies a revision of the pedagogical landscape in terms of the ways in which students engage in learning, and how understandings emerge. In this chapter we consider how the availability of digital technologies has allowed intended learning trajectories to be structured in particular forms and how these, coupled with the affordances of engaging mathematical tasks through digital pedagogical media, might shape the actual learning trajectories. The evolution of hypothetical learning trajectories is examined, while the transitions learners make when traversing these pathways are also considered. Particular instances are illustrated with examples in several settings.