Season 2 · Episode 1913
AI Context Windows Are Junk Drawers
Stop paying for old messages. Here's how to keep your AI sessions clean and on-topic.
My Weird Prompts · Daniel Rosehill
April 2, 202627m 59s
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Show Notes
We explore the hidden engineering challenge of session management in AI interfaces. Learn why stateless APIs struggle with stateful human conversation, causing context pollution, lost-in-the-middle failures, and rising token costs. We cover deterministic fixes like timeouts and commands, smarter architectural patterns using summaries and metadata, and the future of autonomous session management in voice and chat agents.