This paper explores the synergy between human cognition and Large Language Models (LLMs), highlighting how generative AI can drive personalized learning at scale. We discuss parallels between LLMs and human cognition, emphasizing both the promise and new perspectives on integrating AI systems into education. After examining challenges in aligning technology with pedagogy, we review AutoTutor-one of the earliest Intelligent Tutoring Systems (ITS)-and detail its successes, limitations, and unfulfilled aspirations. We then introduce the Socratic Playground, a next-generation ITS that uses advanced transformer-based models to overcome AutoTutor's constraints and provide personalized, adaptive tutoring. To illustrate its evolving capabilities, we present a JSON-based tutoring prompt that systematically guides learner reflection while tracking misconceptions. Throughout, we underscore the importance of placing pedagogy at the forefront, ensuring that technology's power is harnessed to enhance teaching and learning rather than overshadow it.
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