Previous intelligent tutoring systems (ITS) and ITS authoring studies predominantly simulated and evaluated artificial intelligence (AI) techniques and cognitive architectures/notions in educational domains. Current research focuses on software design that is priori driven by educational theories; it concerns the conception of Augmented Conversation and Cognitive Apprenticeship Metamodel (ACCAM). The pedagogy driven metamodel?ACCAM?forms the basis for a formal (theory based) approach to designing ITS authoring tools for numerical aspect of numerical disciplines. This research, therefore, showcases the convergence of two theoretical perspectives—the Conversation Theory (CT) and Cognitive Apprenticeship (CA)—which were never considered together before now. The novel conceptual platform?the ACCAM—flows and benefited from the synergistic effect of the stated theories through the introduction of the concept of ‘augmented conversation’ within the resulting integrated framework. Thus, current work draws on the pedagogical import of the mentioned educational theories, elicits new meanings, and lays the foundation as well as opens future evaluation of a pedagogical engineering methodology that flows therefrom.