Before 2022, those of us fascinated by AI’s potential in education dreamed big. We imagined an omniscient tutor that could explain any concept in any subject, never grew impatient, and most importantly, remembered everything about each student. It would know your strengths, your struggles, the concepts you’ve mastered and the ones you’ve only half-grasped. It would gently guide you, adapt to you, and grow with you. We imagined a mentor that learned you as you were learning with it.
Only part of that vision has arrived.
Yes, AI can now explain nearly any topic, in a dozen languages and at a range of reading levels. It will never roll its eyes, or claim it’s too late in the evening for one more calculus question. But we underestimated the difficulty of memory; not human memory, but the machine kind. Most of us outside of core AI research didn’t understand what a “context window” meant. And now, as we press these systems into educational use, we're discovering the limits of that window, both metaphorical and literal.
ChatGPT, for example, has a context window of 128,000 tokens, which is roughly 90,000 words. Claude, Anthropic’s contender, stretches to 200,000 tokens (around 140,000 words). Grok 4 boasts 256,000 tokens, maybe 180,000 words. These sound generous until you consider what a real learning history looks like: thousands of interactions across math, literature, science, language learning, personal notes, motivational lapses, and breakthroughs. Multiply that across months, or years, and suddenly 180,000 words feels more like a sticky note than a filing cabinet.
AI tools handle this limit in different ways. Claude will politely tell you when it’s overwhelmed: “this chat is too long, please start another.” ChatGPT is more opaque; it simply starts ignoring the earlier parts of the conversation. Whatever is lost is lost quietly. One moment it knows your aversion to visual analogies, and the next it’s offering one as though for the first time. It’s like having a tutor with severe short-term memory loss.
There are workarounds. You can download your long chats, upload them again, and have an AI index the conversation. But indexing creates its own problems. It introduces abstraction: the AI may recall that you're dyslexic, but forget which words you tend to stumble over. It might remember that you needed help with decimals, but not the specific analogy that finally made sense to you. Indexes prioritize metadata over experience. It's not remembering you, it’s remembering notes about you.
So the dream of individualized, adaptive learning, the one we pinned to the emergence of large language models, has only half-arrived. The intelligence is here. The memory is not.
Where does that leave us? Not in despair, but in the familiar terrain of workarounds. If AI can’t yet remember everything, perhaps it can help us do the remembering. We can ask it to analyze our chats, extract patterns, note learning gaps, and generate a profile not unlike a digital learning twin. With that profile, we can then build or fine-tune bots that are specialized to us, even if they can’t recall our every past word.
It is a clunky solution, but it points in the right direction. Custom tutors generated from distilled learning paths. Meta-learning from the learning process itself. Perhaps the next step isn’t a single all-knowing tutor, but a network of AI tools, each playing a role in a broader educational ecosystem.
Is anyone doing this yet? A few startups are tinkering on the edges: some focus on AI-powered feedback loops, others on personalized curriculum generation, and a few are exploring user profiles that port across sessions. But a fully functional memory layer for learners, one that captures nuance over time, across disciplines, is still unattainable.
Maybe the real educational revolution won’t come from making smarter AI, but from getting better at structuring the conversations we have with it. Until then, your AI tutor is brilliant, but forgetful.
AI in Society
Opinions and positions expressed in this blog are mine, and do not represent my employer's opinions or positions. I also have a blog on life in Academia
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