EPISODE · Jul 7, 2026 · 30 MIN
Why Your AI Can't Find That Email
from My Weird Prompts
You ask your AI to find a quote in Gmail, it comes back empty, and the real reply is three threads down. This isn't a failure of AI reasoning — it's a failure of infrastructure. We dig into why Gemini and ChatGPT can't reliably read your inbox, what MCP actually does and doesn't solve, and why the gap between a working prototype and a production-grade integration is filled with unglamorous problems like OAuth token refresh collisions and rate limit pagination.
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Why Your AI Can't Find That Email
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