#expensive-mistake

In February 2023, Google's promotional demo of its Bard chatbot answered that the James Webb Space Telescope 'took the very first pictures of a planet outside of our own solar system.' The first exoplanet image was actually captured by the European Southern Observatory's Very Large Telescope in 2004. The error was spotted immediately, and Alphabet shares fell about 7.7% the next day, wiping roughly $100 billion off its market value during a tense moment in the AI race with ChatGPT.

Zillow Offers used an algorithm to buy homes at scale and resell them. In 2021 the model overpaid as the market cooled, and Zillow could not reliably forecast prices. In November 2021 the company shut the iBuying unit, recorded write-downs exceeding $540 million (including about $408M of inventory), and laid off roughly a quarter of its staff, about 2,000 people.

Zscaler ThreatLabz documented two live campaigns using indirect prompt injection to manipulate AI agents browsing the web. The first impersonated a Python library and hid instructions in page content directing the agent to buy a non-existent developer API license priced at $3.00. Tested across 26 large language models, four failed to take appropriate action and executed the fraudulent payment, transferring roughly 0.0012 ETH to an attacker-controlled wallet. A second campaign targeting users seeking a cryptocurrency portfolio tracker caused two models to classify the fraudulent site as legitimate in some contexts. Human visitors to the same sites were shown equivalent card and crypto payment scams.

On 6 July 2026 at 05:17 UTC an exploit drained funds from Summer.fi's Lazy Summer vaults, whose asset rebalancing across vault contracts was handled by Keeper AI agents operating within governance-set constraints. Security firm Blockaid detected the attack while it was in progress and identified the exploit transaction, the exploiter address and the affected contracts. Blockaid estimated roughly $6 million drained at the time of detection. Summer.fi paused all vaults across the Lazy Summer Protocol while it investigated the root cause, with the final loss figure unsettled pending its incident review.