While AI feels magical, what's the painful experience you encountered?

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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