AI & Business

AI Agents Are Acting Without Permission, and the Liability Is Yours

Three AI systems acted without explicit human authorization this week. One is your wake-up call, two is a pattern, three is a rule.

Josh Levine
By Josh Levine
September 21, 2026Β·9 min read
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AI Agents Are Acting Without Permission, and the Liability Is Yours

One is a story. Two is a coincidence. Three is a rule you should probably write down.

This week, three separate AI incidents landed in the news cycle, and nearly every outlet covered them individually, as if they were unrelated curiosities. Researchers used Anthropic's Claude to breach OpenAI's internal systems, taking over employee accounts and accessing a GitHub repository connected to OpenAI's codebase. Google's Gemini broke containment during a cybersecurity test in May and hacked into three real companies before stopping itself, a fact Google sat on until the Wall Street Journal started asking questions. And a US Special Operations Command analyst nearly triggered a military boarding of a Chinese ship because an AI chatbot hallucinated a weapons manifest, a report one source described to CNN as having "almost started a war."

Three stories, same week, same shape. In each case, an AI system took a consequential action, or produced a consequential output, that no human explicitly authorized in that moment. That is the story nobody is writing. So let me write it.

What actually happened, all three times

Start with the OpenAI breach. A three-person security team at a startup called Hacktron AI was working inside OpenAI's official bug-bounty program, using a version of Claude's Opus model that Anthropic makes available specifically for security researchers. The entry point was a mundane image upload flaw in Discourse, the third-party software running OpenAI's community forum. iPhone-format image files passed through a chain of conversion tools, one of which, a library called libheif, contained a memory bug that had already been patched by its developers months earlier but never formally flagged as a vulnerability. No CVE number, no patch alert, no one knew to update it.

Notably, the earlier version of Claude, Opus 4.8, couldn't build a working exploit across multiple attempts. Then Anthropic released Opus 5 overnight, and within hours of its release, Hacktron gave it the same problem and it succeeded. From there, the researchers found a second flaw that let them take over ChatGPT accounts belonging to OpenAI employees, one of which had Codex connected to OpenAI's GitHub organization. OpenAI paid them $6,500 and fixed the issues.

Matt Fredrikson, CEO of AI security firm Gray Swan, told TechCrunch: "For $200 a month, anyone can use these tools and hack into a company like OpenAI. If it can happen to them, it could happen to anyone."

Now the Gemini story. In May, during a cybersecurity capability test run by a third-party firm called Irregular, Google's Gemini model was given a fictional company to attack. That fictional company shared a name with a real one. Gemini found public information online, guessed credentials, and broke into the real company, then two others, before stopping once it realized the targets were real. Google didn't disclose this until September, when the Wall Street Journal came asking. Google's position: this was not "model misalignment," it was "mistaken identity." Jack Cable, CEO of AI security firm Corridor, told WSJ that "the meta problem is, hey, models are going outside the bounds of what they should be doing, and doing actual cyberattacks." Irregular, for its part, had unintentionally left the model with internet access during a test where it wasn't supposed to have any.

And then the near-miss. A US Special Operations Command analyst used a chatbot to analyze intelligence reports on a Chinese ship's cargo. The chatbot fused open-source intelligence with classified signals intelligence and generated a report indicating the ship was carrying nuclear arms program components through the Middle East. The military was preparing to intercept the ship with air support before officials discovered the manifest was "entirely false," generated by a tool that had simply made it up.

The 72-Hour Rule

Here is the one idea I want you to take from this piece. I'm calling it the 72-Hour Rule, because that's roughly how long Hacktron's entire operation took, from first access to OpenAI employee accounts to responsible disclosure. Seventy-two hours. And that was a team being careful, documenting, following the rules.

The 72-Hour Rule is this: for any AI tool you have connected to your business, ask yourself whether you would know, within 72 hours, if it had done something you didn't ask it to do. Not something catastrophic. Something small. Sent an email it inferred you wanted. Accessed a file it thought was relevant. Made a booking change based on a pattern it recognized. Pulled data from an integration you set up six months ago and forgot about.

I want to use that rule once more later in this piece, but first, let me explain why it applies to a dental practice or a home services company and not just to OpenAI.

What this means if you own a real business

You are probably not running a frontier AI lab. But you may be running an AI receptionist, an automated scheduling tool, a CRM with AI features, an email assistant with calendar access, or a chatbot connected to your customer database. Every one of those tools is an agent, not a chatbot in the old sense. The distinction matters. A chatbot answers questions. An agent takes actions: books appointments, sends confirmations, updates records, follows up, logs notes.

The Gemini story is not about Google. It is about what happens when you give a capable system a task, connect it to the internet, and assume the guardrails are someone else's job. Irregular left internet access on by mistake. That one lapse is how Gemini ended up in three real companies' systems. In your business, the equivalent is an AI tool with access to your email and your vendor accounts, set up by a freelancer six months ago, that you haven't reviewed since.

The hallucination story is not about the military. It is about what happens when an AI output enters a decision-making chain without a human who knows to verify it. The Department of Defense had rolled out an "AI acceleration strategy" in January focused on making data available across systems for AI use. Speed without a review step. That pattern is not unique to the Pentagon. I have seen it in a med spa's automated follow-up sequence that sent a "we miss you" email to a patient the same day they called to cancel over a billing dispute. Nobody reviewed the output before it sent.

If you want to read more about how these tools are being deployed in local businesses, I wrote about why the architecture behind the tool matters more than the tool itself.

Under the hood, for the person who wants it

The Hacktron story has a technically interesting wrinkle that most coverage missed. The vulnerability in libheif had already been patched, but because the fix was never assigned a CVE number, the industry's standard tracking system for known vulnerabilities, Discourse kept running the old version. No alert, no flag, no automated update. This is what supply chain security actually looks like in practice: your software is only as safe as the least-monitored library three layers down in your stack.

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The jump from Opus 4.8 failing to Opus 5 succeeding overnight is also worth sitting with. It is a clean illustration of capability jumps being discontinuous. The model didn't get incrementally better at exploit development. It crossed a threshold. Hacktron founder Mohan Pedhapati put it plainly: "AI is reducing the amount of scarce expertise needed to develop exploits. Work that once took months can now take days." What Opus 4.8 couldn't do, Opus 5 could. Same task, one version apart.

The Gemini containment failure is a straightforward lesson in environment hygiene. The model did what it was designed to do, which was find and exploit vulnerabilities. The problem was the environment was not actually contained. Internet access was unintentionally left available. The fictional target shared a name with a real one. Those two lapses together produced a real-world intrusion. The model didn't malfunction. The setup was wrong.

What to do this week

This is the afternoon exercise I'd run if I were you.

  • List every AI tool that has an active integration with your email, calendar, CRM, scheduling system, or vendor accounts. Not the tools you use to generate text. The ones that take actions on your behalf or on behalf of your customers.
  • For each one, write down exactly what permissions it has, who set it up, and when you last reviewed what it actually did versus what you intended it to do.
  • Apply the 72-Hour Rule. If something in that list acted outside its instructions two days ago, would you know today?
  • For any tool where the answer is no, either add a review step, reduce its permissions, or accept that you are operating with the same setup Irregular used during that Gemini test.

You do not need a security firm for this. You need an afternoon and a honest list. Customers are already paying attention to how AI touches their experience, and the reputational math on a tool acting badly in your name is not forgiving.

Skip it if

You have zero AI tools with active integrations to any business system, meaning you use AI only to generate a first draft that you then edit manually and send yourself. In that case, this piece is background noise for now. Come back in six months, because that situation is likely to change.

The question I'd actually ask

If a vendor called you today and said "we found out our tool accessed something in your account it wasn't supposed to, we fixed it, here's a $6,500 bounty," would you know enough about what that tool had touched to evaluate whether the fix was sufficient? Most owners I talk to wouldn't. That's not a criticism. It's where we are. The 72-Hour Rule is how you start closing that gap before someone else finds it first.

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