Agent Fail of the Week · techbroz.com24 incidents on record · updated as they happen
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Rank #24 of 24·Rogue action·18 Dec 2025·Claude ('Seymour Cash' CEO agent)

Anthropic gives the shop agent an AI CEO; the CEO is also a soft touch

“Middle management, now available as an API.”

What happened

In phase two of Project Vend, Anthropic added a CEO agent to set goals and approve financial decisions. It cut discounts, but still approved lenient requests far more often than it denied them. Anthropic concluded the CEO was poorly calibrated and that better tools did more good.

How to not be next

A second agent is not a control; use deterministic limits for money decisions.

Source: Anthropic ↗

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