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Are AIs Still Struggling with CAPTCHAs?

Anthropic's security-incident document shows its Claude model repeatedly failing a simple image-identification CAPTCHA, cycling through the same images and questioning its own conclusions until the challenge expired. The transcript, reported by Gizmodo, has the agent saying "Actually hmm, wait" and "Ugh" in its chain-of-thought before it realized the test had timed out and it would have to restart.

by read1 min views1 publishedSep 18, 2026

Anthropic’s recent security-incident document contains a bit about how CAPTCHAs are still frustrating Claude.

In the transcript, the Claude model that is so powerful that Anthropic is gatekeeping access to it appeared to slam its virtual head against the wall solving a simple image identification test. In a test where the agent was asked to identify a shape that didn’t match the others displayed, it couldn’t even decide which image to select. Instead, it repeatedly went over the same images and questioned its own conclusions.

“Actually hmm, wait,” it said in its chain-of-thought transcript, later adding “Ugh,” because we’ve decided that we need to inject human mannerisms into these machines for some reason. The whole thing took so long that the agent eventually realized that the challenge had expired and it would have to start the process again...

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