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We study the problem of troubleshooting machine learning systems that rely on analytical pipelines of distinct components. Understanding and fixing errors that arise in such integrative systems is difficult as failures can occur at multiple points in the execution workflow. Moreover, errors can propagate, become amplified or be suppressed, making blame assignment difficult. We propose a human-in-the-loop methodology which leverages human intellect for troubleshooting system failures. The approach simulates potential component fixes through human computation tasks and measures the expected improvements in the holistic behavior of the system. The method provides guidance to designers about how they can best improve the system. We demonstrate the effectiveness of the approach on an automated image captioning system that has been pressed into real-world use.