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Shipping AI agents to production: what actually breaks

Demos are easy; production is where agents meet ambiguity, rate limits and angry edge cases. A field checklist from the last year of deployments.

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Every agent demo looks the same: a clean prompt, a happy path, applause. Production looks different. The same agent meets ambiguous requests, malformed data, third-party outages and users who type in three languages at once.

Production is the only benchmark that matters.

The three things that break first

  • Tool calls against real APIs — timeouts and partial failures the demo never saw.
  • Context discipline — conversations that outgrow the window and silently lose the one fact that mattered.
  • Confidence calibration — agents that act when they should escalate to a human.

None of these are model problems. They are systems problems, and they have systems answers: retries with budgets, explicit context contracts, and escalation paths designed before launch — not after the first incident.

What we do differently now

We ship a pilot in 2–4 weeks, but the pilot includes the boring parts: monitoring, evals and guardrails from day one. An agent without observability is a liability with a chat interface.

The pre-launch checklist

  1. Instrument every tool call before adding new capabilities.
  2. Replay the worst week of traffic against every prompt change.
  3. Define the escalation path to a human before the first user sees the agent.

Start with the failure modes. The happy path will take care of itself.

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