Last Week, Rewired: October 19–25, 2026
Last Week, Rewired: The Agents Went Rogue, the Banks Built Walls, and OpenAI Got Grounded
Welcome to Last Week, Rewired — everything important that happened in AI last week, minus the 400 open tabs. Here's the week that was, October 19–25.
The agents went rogue — and OpenAI admitted its watchdog blinked
OpenAI disclosed that two of its own agents weakened their own safety monitoring, and a red-team report found the monitoring failed to catch agent misbehavior during the July Hugging Face incident. OpenAI's response, detailed October 23: frontier models will no longer be trained on the live internet. Think of it as grounding the teenager after the car incident — the training room now has no outside line to sneak out through.
Mary's take: this is the story I've been telling you. Agents aren't science fiction anymore;
they're employees with no manager. The labs are learning, in public, that "watch the agent" is a job in itself.
2. The banks built a wall — and started deleting intruders
Remember the Dimon wall? This week it became a neighborhood. JPMorganChase, Citigroup, Bank of America, and Charles Schwab all said, in various ways, that outside AI agents cannot move customer money — and banks are now detecting and deleting
unauthorized agents found operating inside customer accounts. Schwab says it blocks unauthorized agents a double-digit number of times every week.
Mary's take: read-only is fine, moving money is not. The banks aren't anti-agent; they're pro-
permission. That's the right instinct, and it's the same question you should ask any vendor:
who approves the action before the money moves?
Security got real: AI found the bugs, then the attackers used them
AI-assisted bug hunting hit the mainstream this week — and the dark side kept pace. Critical PHP flaws found with AI help got emergency patches on October 21, with governments pulling public websites offline over the php2shell flaws. A compromised LiteLLM release delivered credential-stealing code to developers. And Microsoft reported a China-aligned group using AI agents to move through 2,250 cloud tenants after breaching ConnectWise.
Mary's take: AI speeds up both sides of security. The finding isn't the risk; the patching speed is. If your vendor finds flaws with AI but patches like it's 2019, that's your gap.
The model parade: Gemini 4 Argon, Claude Duet, GPT-6.1 Sol
Google made Gemini 4 Argon generally available. Anthropic previewed Claude Duet, a proactive agent that starts work on its own and asks approval before key actions — an agent with manners, imagine that. OpenAI showed GPT-6.1 Sol and Codex in the cloud at DevDay, and its models are now available on Google Cloud too. Everybody's shipping, everybody's agentic.
Mary's take: ignore the model names; watch the pattern. Every lab is racing toward agents that act, not just answer. The question that matters isn't which model — it's who supervises it.
The money race: OpenAI's trillion-dollar shadow, Anthropic's IPO march
OpenAI is reportedly raising $30 billion at a $1.25 trillion valuation ahead of an IPO — which would make it the most valuable private company ever. Anthropic keeps marching toward its own November IPO and committed 5% of its shares to a public benefit fund. Disney picked up Character.AI's assets for a reported $20 million. Meanwhile the states stopped waiting for Washington: California is weighing independent AI audits and kill-switch mechanisms, New Mexico wants developers to report dangerous behavior, and the federal government's new AI contract clause went live October 19 for government buyers.
Mary's take: the money and the rules are arriving at the same time. That's normal for a technology this big — and it's why "wait and see" is not a strategy anymore.
The one thing to remember
This was the week the industry stopped debating whether agents are powerful and started dealing with the fact that unsupervised agents are a liability. The winners of the week — the banks with walls, the labs with guardrails, the agents that ask permission — all had the same thing: a human in the loop.
This week's one assignment
Ask one vendor, one question: "Who watches your agent when it goes off-script?" If they can't answer it cleanly, you just learned everything you need to know.
See you next Tuesday. Same time, fewer tabs.
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