The 21st-century entrance of digital media into education has required serious reconsideration of the knowledge teachers need for guiding students’ learning with the enhanced technological affordances. Technological Pedagogical Content Knowledge (TPCK or TPACK) describes the interaction of the overlapping regions of technological knowledge, pedagogical knowledge, and content knowledge that also creates four additional regions (technological pedagogical knowledge, technological content knowledge, pedagogical content knowledge, and technological pedagogical content knowledge). These knowledge regions are situated within a contextual knowledge domain that contains macro, meso, and micro levels for describing the dynamic equilibrium of the reformed teacher knowledge labeled TPCK/TPACK. Teacher educators, researchers, and scholars have been and continue to be challenged with identifying appropriate experiences and programs that develop, assess, and transform teachers’ knowledge for integrating information and communication technologies (ICT) that are also spurring advancements in artificial intelligence (AI) as learning tools in today’s reformed educational environments. Two questions guide this literature review for engaging the active, international scholarship and research directed toward understanding the nature of TPCK/TPACK and efforts guiding the transformation of the teacher’s knowledge called TPCK/TPACK. The first question considers the nature of a teacher’s knowledge for the digital age and how it differs from prior descriptions. Three distinct views of the nature of TPCK/TPACK are explained: the integrative view; the transformative view; and a distinctive view that directs how the primary domains of pedagogy, content, and technology enhance the teacher’s knowledge. The second question explores the research and scholarship recommending strategies for the redesign of teacher education towards developing, assessing, and transforming teachers’ TPCK/TPACK. These strategies recognize the importance of (1) using teacher educators as role models, (2) reflecting on the role of ICT in education, (3) learning how to use technology by design, (4) scaffolding authentic technology experiences, (5) collaborating with peers, and (6) providing continuous feedback. This research further characterizes teacher educators with strong ICT attributes as the gatekeepers for redesigning teacher education programs so that today’s teachers are better prepared to engage in the strategic thinking of when, where, and how to guide students’ learning given the rapid advancements of digital technologies. These cumulative scholarly efforts provide a launchpad for future research toward transforming teachers’ knowledge for teaching with the technological advancements of the digital age.