This paper is concerned with identifying and assessing the impacts of various technologically enriched approaches to mathematics learning. Its purpose is to address the usefulness of emerging knowledge to enhance practice, and to contribute to theorizing about technology-based learning. Hence the main drivers are intentions to identify and elaborate on obstacles, errors, and unresolved problems on the one hand, and positives and insights on the other. The paper tells a cautionary tale about expectations of technology-enhanced learning, while simultaneously uncovering a rich base from which to theorize and test new appreciations of what is involved when students, technology, and mathematics connect in learning settings. A summary assessment is that this area still very much represents work in progress, but there is now a heightened realization, at least among those not transfixed by technological blindness, that the search for ultimate answers will require much greater exploration of machine-mathematics-learner relationships.