How might understanding emerge when learners engage mathematical phenomena through digital technologies? This paper considers the ways children's mathematical thinking was influenced by their interpretations through various pedagogical discourses and how understanding emerged through those various filters. Current research into using digital technologies in mathematics education is predominantly positioned within two theoretical perspectives, semiotic mediation and the instrumental approach. Meanwhile, within a contemporary hermeneutic position, mathematical learning comprises a process of interpretation, where understanding is seen as a formative process as the learner views events from fresh, ever-evolving perspectives. Concepts are then seen in ongoing formation. This paper examines learning through a contemporary hermeneutic frame and the contention is that this opens opportunity for learning to be perceived in alternative ways.