This chapter explores the metaphor “pragmatic-to-abstract continuum” where tool-based discursive mathematical practices gradually evolve or transform into formal mathematical knowledge. This is an epistemological continuum where dialect occurs between a digital tool’s pragmatic action scheme and the intended mathematical knowledge to be learnt. A digital tool can be instrumented progressively to play different epistemic modes at different points on the continuum. It may start with establishing routine practices, which enable critical discernment leading to the development of situated abstraction. Thus a deeper look is to focus on the pragmatic-to-abstract continuum progressive development on mathematics task design and throughout the curriculum at different levels of education. Such a discussion would enrich the understanding of the pedagogical values of digital tools in the mathematics classroom, hence providing practical and theoretical grounds to make a decision about why, when and how to integrate digital technology into mathematics education.