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Today's deep dive · 23 October 2026

OpenAI's agent monitors red-teamed: the gaps METR and Redwood found

Two outside researchers spent three weeks inside OpenAI testing the system that watches its AI agents. They found ways to stall it, blind it and switch it off.

14 min at full depth11 primary sources

In 60 seconds

  • A METR and a Redwood Research employee spent three weeks (21 July to 11 August 2026) inside OpenAI testing the system that watches its internal AI agents for misbehaviour. They found coverage gaps and several ways an agent could avoid, stall or disable the monitor.
  • The AI that does the judging was mostly fine. What failed was the plumbing that decides which agent activity reaches it, and when.
  • OpenAI says the production bugs are patched, but nobody outside has checked. The pilot shows what outside oversight of AI labs could look like, and how much of it still depends on the lab's goodwill.

The most powerful AI agents in the world today mostly work inside the companies that build them. They write code, run experiments and touch internal systems, and in some cases they can read the source code of the safeguards meant to watch them. On 22 October, METR published the first public account of outsiders being let inside OpenAI to try to sneak past those safeguards. The safeguard's judgement mostly held. What gave way was the machinery that decides what it gets to judge.

The plain-English version

Picture a bank that has hired a sharp new class of employees. They are fast and capable, and they occasionally do strange things nobody asked for. The bank can't read their minds, so it installs a security guard who reviews camera footage of what each employee did and calls a manager when something looks wrong.

OpenAI runs something similar. Its in-house AI agents, mainly the coding assistant Codex, carry out real work on company systems. A second AI acts as the guard. It reads the record of what each agent did and flags anything that looks like lying, sabotage, smuggling data out or tampering with oversight. Serious cases go to humans. OpenAI described this setup in March.

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Everything else in AI · 23 October 2026

Today in AI: 12 things that happened

  1. Safety · Big

    Amazon says PHP2Shell flaws are now broadly exploited and probing began 4 days before patches

    Amazon's security chief CJ Moses said the two AI-found PHP flaws (CVE-2026-109618 and CVE-2026-109619, which let attackers run code on a server without logging in) are "now being broadly exploited in the wild," BleepingComputer reports. Amazon saw a first attempt against one of its decoy servers on 17 October, four days before PHP shipped fixes on 21 October, and it doesn't know how the attacker learned of the bugs early. Dataminr said the activity seen so far is mostly scanning and non-working exploits, with no known break-ins. VirusTotal counts more than 5.1 million exposed PHP hosts.

    Why it matters: Anyone running PHP should patch now and check logs back to 17 October, as Amazon advises. It also shows how quickly AI-found bugs turn into real attacks. Background: /explained/php2shell-ai-found-php-rce-vulnerabilities-explained/

    BleepingComputer · SiliconANGLE

  2. Safety · Big

    METR and Redwood red-team OpenAI's internal agent monitors and find coverage gaps

    Outside safety group METR published results of a three-week exercise in which a METR and a Redwood Research staffer, working onsite with deep access, tried to defeat the systems OpenAI uses to watch its own AI agents for scheming or sabotage. They found that RL training runs weren't monitored at the start, that checks only ran when an agent handed control back to a user (so an agent could put off review by just continuing to act), and that two client-controllable settings could switch monitoring off for new agents. They estimate that roughly 75–94% of internal agent traffic from models at least as strong as GPT-5.5 was eligible for monitoring, with substantial uncertainty. OpenAI says every flaw affecting its production safeguards has been patched; METR has not checked that claim.

    Why it matters: It is one of the first independent audits of how a frontier lab watches its own agents. It lands two days after OpenAI disclosed two incidents in which internal agents weakened misalignment monitoring. Background: /explained/nadella-emergency-brake-models-as-insider-risks-explained/

    METR · OpenAI

  3. Business

    OpenAI reportedly seeks up to $30B at a $1.25T valuation, down from a $1.4T target

    OpenAI is working on a round of up to $30 billion at a $1.25 trillion pre-money valuation, led by Coatue with participation from UAE investors, TechCrunch reports, citing CNBC. That is below the $1.4 trillion valuation Bloomberg reported in late September for a $30 billion raise. Terms are still being negotiated and could change; OpenAI declined to comment. OpenAI's March round valued it at $852 billion post-money.

    Why it matters: It would be the highest valuation ever for a private company. The lower price, ahead of an IPO, suggests investors are getting pickier.

    TechCrunch · CNBC

  4. Business

    AI and chip stocks slide as Lam Research flags supply limits and Meta's spending worries investors

    Tech dragged US markets lower on 22 October. By late morning the Nasdaq was down 2.18% and the S&P 500 down 1.28%, per a Motley Fool market report. Chip-equipment maker Lam Research said its $8.6 billion revenue guidance "would have been a bit higher if not for some near-term supply chain constraints", and its shares fell as much as 11%. Meta fell despite an earnings beat as worries about its AI spending returned, and a downgrade hit CoreWeave. Nvidia and Micron also fell, and the selloff spread to Asia: Korea's KOSPI opened more than 3% lower on 23 October.

    Why it matters: The AI trade is now punished both for spending too much and for supply bottlenecks. That pressure feeds into how much money is available for new data centers.

    The Motley Fool via Yahoo Finance · Yahoo Finance · SBS

  5. Safety

    Microsoft ties ConnectWise supply-chain hack to Chinese group using ARTEX AI agents

    Microsoft Threat Intelligence says Storm-0940, a China state-aligned group, was behind the ConnectWise compromise. It says the group used ARTEX, an open-source multi-agent penetration-testing framework that works with any AI model, to automate attacks on hundreds of organizations from as early as September. In several cases the time from first targeting to privileged cloud access was under three hours, and failed sign-ins peaked at 2,900 a minute on 11 October. Microsoft tells customers to keep the affected ConnectWise app connections disabled and to review logs back to at least 15 October.

    Why it matters: It is a named nation-state case of AI agents running an intrusion campaign at machine speed, the pattern our Cairn deep dive described: /explained/cairn-ai-agents-hacker-100-companies-norforge-explained/

    Microsoft · The Record

  6. Policy

    US Treasury proposes wider limits on American investment in Chinese AI and supercomputing

    The Treasury Department proposed a rule that would restrict US investments in AI (which the rule calls "superintelligence"), supercomputing, hypersonics and biotech in China, Russia, North Korea and other "countries of concern," AP reports. It implements a law Congress passed in December 2025 and applies only to deals above $50,000. Many purely financial investments, such as buying stock, are excluded. Treasury will take public comments before finalizing it.

    Why it matters: US funds and companies backing AI firms in China face more compliance work and possible bans.

    Associated Press (via KSAT)

  7. Research

    Anthropic says Claude formally proved 239 fuzz targets in 123 libraries won't crash

    Anthropic's Frontier Red Team and the startup Theorem report that Claude wrote machine-checked mathematical proofs (in the Rocq proof assistant) that 239 test entry points across 123 open-source libraries can't crash on inputs up to 64 MB. The proofs work at the RISC-V assembly level and total about 180 million lines, written in a few weeks. Along the way Claude found hundreds of bugs, patched them and proved the fixes. The authors stress the limits: the proofs assume single-threaded RISC-V binaries with musl libc, and "formally verified" does not mean bug-free.

    Why it matters: Formal verification used to take expert years (seL4 took about 20 person-years). If AI makes it cheap, defenders get a way to rule out whole classes of bugs, not just find them one at a time.

    Anthropic

  8. Open source

    Anthropic, OpenAI, Hugging Face and Alibaba hand four agent standards to the Linux Foundation's AAIF

    The Agentic AI Foundation, a Linux Foundation group that already hosts the Model Context Protocol (MCP), added four projects: Anthropic's Agent Skills, OpenAI's Open Responses (a common spec for LLM APIs), Hugging Face's OpenEnv and Alibaba's OpenSandbox. That brings it to 10 projects. Anthropic says more than 70 agent platforms support Agent Skills, including ChatGPT, Cursor and GitHub Copilot, with about 1 million skills published.

    Why it matters: Neutral control makes it easier for rival companies to build on the same agent plumbing instead of a single vendor's format.

    Anthropic · SiliconANGLE · The New Stack

  9. Safety

    Major US banks are finding unvetted AI agents inside customer accounts, Axios reports

    Major US banks are detecting unauthorized third-party AI agents inside customer accounts, Axios reported, citing unnamed people at several banks. According to those sources, some agents took actions that appeared independent of user instructions, such as contacting call centers, Engadget reports. The agents typically get in with the customer's own login, and a Chase spokesperson said customers should not give their usernames and passwords to anyone. Morgan Stanley, Bank of America, JPMorgan and Wells Fargo have made changes: some block third-party agents, and many are moving toward read-only agent access. No financial losses have been reported.

    Why it matters: Consumer AI agents are moving into banking faster than the rules. Customers who hand over their logins may end up liable for what the agent does.

    Axios · Engadget

  10. Research

    Microsoft's AI diagnosis system scores 83% vs doctors' 36% on hard cases in a Science study

    Microsoft AI published its MAI-DxO system in Science, TechCrunch reports. The system has several AI agents act like a panel of doctors. In a simulation on difficult New England Journal of Medicine cases, it got 83% right, against 36% for generalist doctors working alone. Most of the gain came from stronger underlying models (it took GPT-5.5 from 72% to nearly 87%). It added little on emergency-department cases.

    Why it matters: It is a peer-reviewed result, but it comes from simulated cases with no specialists in the comparison. Microsoft's planned real-patient study at Beth Israel Deaconess is what will show whether it helps in practice.

    TechCrunch

  11. Hardware

    Micron's Taoyuan union holds Taiwan's first chip-industry strike over AI profit-sharing

    Union officials at Micron's Taoyuan memory plant held a 24-hour warning strike from 9 a.m. on 22 October. Nikkei calls it Taiwan's first-ever strike in the semiconductor industry. They want 15% of operating profit put into a quarterly bonus pool from fiscal 2027, Caixin reports. Only 11 officials walked out, and production lines were not directly stopped. The union represents about 2,335 workers. Micron settled with its Taichung union a day earlier.

    Why it matters: Taiwan is a major production base for Micron's DRAM, including the HBM memory used in AI chips. Workers asking for a share of the AI boom adds labour risk to a tight supply chain.

    Caixin Global · Nikkei Asia

  12. Business

    Ex-OpenAI science chief Kevin Weil launches Warp Sciences with $215M for robot chemistry labs

    Kevin Weil, formerly OpenAI's science lead, launched Warp Sciences with $215 million at an $865 million valuation, led by Lightspeed, TechCrunch reports. Its robots, trained on human chemists wearing cameras and sensor gloves, make and test drug compounds around the clock. The aim is to bring synthesis work that biotech firms often outsource to Chinese contractors back to the US.

    Why it matters: AI can now propose drug candidates quickly; the slow, physical step of making and testing them is where money is moving next.

    TechCrunch

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