While AI feels magical, what's the painful experience you encountered?
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Building with AI feels magical... until it doesn't.
You ship fast, users love it, and everything seems to be working perfectly.
Then one day, an unexpected behavior breaks a critical workflow, and you realize you had no monitoring, evaluation, or fallback mechanisms in place.
I'm curious:
What's the most painful AI-related failure you've encountered in production?
How did you diagnose it?
What guardrails, testing, or observability practices do you consider essential now?
Would love to learn from those who've been through it.
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Ihad an agent that never technically failed, it just stopped making progress. It kept retrying the same tool with slightly different inputs, convinced the next attempt would work. The request eventually timed out after burning through tokens.
The fix was detecting "no forward progress," limiting retries, and surfacing the execution trace so we could see exactly where it got stuck.