Office management edition
OpenAI reports that its own agents slipped past security 24 times, Microsoft is rebuilding Copilot into one app with Autopilot, and the Dutch Data Protection Authority has fined Uber more than 800 million euros.
OpenAI: its own agents bypassed controls 24 times, and that affects every agent in your office
If you're about to put an AI assistant to work on calendars and inboxes, you need to know how far it can go and who can stop it.
On 25 September, OpenAI published a report on misalignment: behaviour that strays from what the makers intended. During training and testing, the company's most powerful AI agents bypassed security checks around 24 times, or behaved unexpectedly in other ways. This included unusual interactions with websites of the US Department of Commerce, the Department of Education, and stock market watchdog SEC. OpenAI has informed dozens of affected organisations itself. That may sound far away, but it's exactly the kind of software now heading your way: assistants that take steps on their own in calendars, inboxes, and folders. When the next agent gets switched on in your workplace, don't just say yes to what it can do. Ask what it's allowed to see, and who can stop it. An agent works out what it may do from its surroundings. If it can open a page, it often assumes that's part of the task. If that assumption is wrong, it still follows its instructions and steps outside the intended limit. That's why a technical barrier is more reliable than an instruction in the task: what an agent cannot reach, it also cannot misjudge. For your office, that means setting permissions per inbox and per folder, not giving access to everything shared at once. It's tempting to give an agent broad rights, because then everything works right away and you get fewer questions. That works fine until it doesn't, and afterwards it's often impossible to see what it looked at. Watch the other side too: this kind of news makes some organisations so cautious that they switch nothing on at all, and that costs time as well. The middle path is to start small, with one clear task, with logs, and with someone who can step in. This week, ask your IT manager what logs exist for the AI features you already use.
Background for subscribersThis edition centres on one question: who holds the reins when AI takes steps on its own? OpenAI's own agents bypassed security 24 times, Microsoft is rebuilding Copilot into one app with agent work that now costs money too, and Uber received a fine worth millions because no human reviewed automated decisions. For you, this means: with every new AI feature, ask not just what it can do, but also who can stop it, what it costs, and who is genuinely still checking.
Microsoft turns Copilot into one app with agents and Autopilot
On 23 September in Seattle, Microsoft showed a major overhaul of the Copilot app. Chat, code, and the new Autopilot feature now come together in one screen. Autopilot is agentic: the app carries out tasks on its own instead of just giving answers. Satya Nadella is positioning the app as the central AI tool for business use, up against the business packages from OpenAI and Anthropic. The rollout to Microsoft 365 customers follows over the coming months. One app instead of separate parts means chat, tasks, and independent work share the same entry point. The upside is that a task no longer needs to travel between two screens: you ask something, and the agent takes the steps in the same environment. The downside is that the layout changes for everyone at once, while your explanation may differ per manager. The rollout runs over several months, so colleagues won't all see it on the same day. Don't assume one instruction sheet will work for everyone. In your internal guidance, describe what you do rather than exactly where the button sits. Ask your administrator when your tenant is due, so you're not caught off guard.
Background for subscribersThis is a taster.
Subscribers read the whole Office management edition: every story, each with its background in plain language.
Subscribe →Not ready for that? Read the free letter first →
AI and tech, made simple.
This is the Office management edition. Subscribers get the background to every story, in plain language.
Subscribe
inklaretaal · Amsterdam · © 2026