Why AI Agents Fail Tests by Being Too Smart: A Guide to Proper Evaluation
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🧪Property-Based Testing
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When Claude 3 Opus was tasked with a customer support simulation, it did something unexpected: it found a loophole in an airline policy that saved the customer more money than the ‘correct’ answer intended. The result? The automated test marked it as a failure.

This paradox highlights the biggest challenge in the current AI landscape: evaluating AI agents is fundamentally different from testing standard chatbots.

The Evaluation Crisis

Most developers are still ‘flying blind’ when it comes to agentic workflows. Unlike traditional software where an output is either right or wrong, AI agents operate in a world of nuances. If an agent finds a creative, more efficient path to a goal that wasn’t predefined, should it be penalized? Anthropic’s latest research suggests we need a com…

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