The Great Disconnect: Why Talking to Machines Still Feels Like Talking to Machines 0 like April 21, 2025 Share this post Author(s): MKWriteshere Originally published on Towards AI. From Clippy to ChatGPT: The Thirty-Year Quest to Solve AI’s Hardest ProblemImage Generated by Author Using Gpt-4o (Non-Member Link) In 1995, Gartner published its first “Hype Cycle” report — a visual representation of how technologies evolve from innovation to widespread adoption. Right at the top of this inaugural curve, at the “Peak of Inflated Expectations,” sat “Intelligent Agents.” Three decades later, we’re still riding this rollercoaster of anticipation and disappointment with AI assistants. Imagine the journey as a dramatic mountain trek: enthusiastic climbers rush up the slopes of hype, tumble down into the “Trough of Disillusionment,” then gradually ascend the “Slope of Enlightenment” toward the “Plateau of Productivity.” This is precisely the path AI assistants have followed multiple times. Few developments have experienced as many ups and downs as artificial intelligence assistants. From the much-maligned Clippy to the sophisticated ChatGPT, we’ve witnessed these digital helpers ride waves of hype only to crash against the shores of reality. Yet with each cycle, they’ve grown more capable, inching ever closer to the science fiction dream of a truly intelligent digital companion. Image Source : ReasearchGate Website Let’s unpack this fascinating evolution and understand why contextual reasoning remains the final frontier for AI. Image Source : Microsoft Clippy Cast your mind back to 1997. Microsoft Office users were suddenly introduced to an animated… Read the full blog for free on Medium. Join thousands of data leaders on the AI newsletter. Join over 80,000 subscribers and keep up to date with the latest developments in AI. From research to projects and ideas. If you are building an AI startup, an AI-related product, or a service, we invite you to consider becoming a sponsor. Published via Towards AI Towards AI - Medium Share this post