Radical constructivists advocate discovery-based pedagogical regimes that enable students to incrementally and continuously adapt their cognitive structures to the instrumented cultural environment. Some sociocultural theorists, however, maintain that learning implies discontinuity in conceptual development, because novices must appropriate expert analyses that are schematically incommensurate with their naive views. Adopting a conciliatory, dialectical perspective, we concur that naive and analytic schemes are operationally distinct and that cultural–historical artifacts are instrumental in schematic reconfiguration yet argue that students can be steered to bootstrap this reconfiguration in situ; moreover, students can do so without any direct modeling from persons fluent in the situated use of the artifacts. To support the plausibility of this mediated-discovery hypothesis, we present and analyze vignettes selected from empirical data gathered in a conjecture-driven design-based research study investigating the microgenesis of proportional reasoning through guided engagement in technology-based embodied interaction. 22 Grade 4–6 students participated in individual or paired semi-structured tutorial clinical interviews, in which they were tasked to remote-control the location of virtual objects on a computer display monitor so as to elicit a target feedback of making the screen green. The screen would be green only when the objects were manipulated on the screen in accord with a “mystery” rule. Once the participants had developed and articulated a successful manipulation strategy, we interpolated various symbolic artifacts onto the problem space, such as a Cartesian grid. Participants appropriated the artifacts as strategic or discursive means of accomplishing their goals. Yet, so doing, they found themselves attending to and engaging certain other embedded affordances in these artifacts that they had not initially noticed yet were supporting performance subgoals. Consequently, their operation schemas were surreptitiously modulated or reconfigured—they saw the situation anew and, moreover, acknowledged their emergent strategies as enabling advantageous interaction. We propose to characterize this two-step guided re-invention process as: (a) hooking—engaging an artifact as an enabling, enactive, enhancing, evaluative, or explanatory means of effecting and elaborating a current strategy; and (b) shifting—tacitly reconfiguring current strategy in response to the hooked artifact’s emergent affordances that are disclosed only through actively engaging the artifact. Looking closely at two cases and surveying others, we delineate mediated interaction factors enabling or impeding hook-and-shift learning. The apparent cognitive–pedagogical utility of these behaviors suggests that this ontological innovation could inform the development of a heuristic design principle for deliberately fostering similar learning experiences.