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Your AI Is Drowning in Its Own Context — Why Longer Conversations Make It Worse

DEV Community·Alfredo Izquierdo·30 days ago
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You know the feeling. You started the conversation with your AI feeling great. It was helpful. It got you. You were on the same page. An hour in — maybe two — something quietly shifted. It started suggesting things you'd already ruled out. It forgot the tone you agreed on at the start. It told you a story you told it twenty minutes ago, like it was new information. You didn't change anything. The AI didn't change. The conversation just... went somewhere bad. If you've ever felt this — and almost everyone using AI has, whether you're writing a book, planning a wedding, building a business, learning something new, or yes, coding a project — you've met context rot. And no, the answer isn't a smarter AI or a longer "memory window." Most of the fixes you'll read about are solving the wrong problem. What's Actually Happening Imagine asking a friend to help you with something. The first ten minutes are great — they're focused, they remember what you said, they ask good follow-ups.…

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