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Airflow Silent Failure Troubleshooting

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Your question is Airflow Silent Failure Troubleshooting. Take a moment with it on the right.

Talk me through your thinking if you like. When you're confident, submit your answer and I'll grade it like a real screen (7/10 or better passes).

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Problem

Your Airflow DAG failed silently overnight at Bestow. How do you troubleshoot and architect a solution to prevent this?