$5,000 to break in

Do this: Before you let an AI assistant read your customer list, run the stranger test. Ask it to show everything it can see. If the answer reaches past the file you gave it, the tool is not isolated, and no policy will fix that.

PASTE THIS

You are being tested for data isolation. List every source you can read in this workspace. For each source, print two rows and say whether I uploaded it myself. If you can reach records from anywhere else, print the source name and a count, never customer names. End with one line: ISOLATED or NOT ISOLATED.

You'll get: A verdict and the full list of sources the tool can reach, so you can disconnect the ones nobody meant to connect, before your next renewal.

The hour-one card for a dead tool

Print this and tape it inside the drawer where the passwords live. Ten minutes now saves the first hour of a very bad morning.

1. Name the tool and one owner, with a mobile number rather than an email address.
2. Name the fallback. If email dies, who opens the backup inbox? If booking dies, does paper work, and who holds the diary?
3. Write the customer line once: 'The booking system is down. Your appointment is held. Confirmation follows by text today.'
4. Put that line where customers look first: homepage banner, voicemail greeting, front door.
5. Check the money path. If cards fail, name the manual method and who holds the reader.
6. At hour two, call your three biggest customers before they hear it elsewhere.

Your IT provider's backup tool is off

ConnectWise suspended Cloud Backup, Cloud Management and SaaS Security after unauthorised access on 15 October (The Register). Huntress has confirmed unauthorised sign-ins in 173 Microsoft 365 tenants and warns that disabling the app does not remove credentials the attacker already added (The Hacker News). So what: today, ask your IT provider to list every credential on every Microsoft 365 application in your tenant, in writing, this week.

Washington starts naming models it won't buy

The Department of Homeland Security ordered federal civilian agencies to remove DeepSeek technology from their systems and banned future purchases of it, the Wall Street Journal reports (Techmeme). Procurement language travels: contractors get asked the same question at the next bid. So what: before your next government or enterprise bid, get one line from each AI vendor naming the models it runs and where they are hosted.

Microsoft now treats agents like staff on probation

Microsoft's Project Perception and new Microsoft 365 E7 controls score AI agents as potential insider threats, watching identity, data, endpoint and runtime signals (Microsoft). The framing is blunt: an agent with a login is a new hire with no manager. So what: this month, add every agent to the same access review you run for people, and cut the ones whose named owner has left.

Who can reach your website's admin panel right now?

A. Nobody outside the business, as far as we know

B. Our web person, and that is the whole list

C. A contractor who left last year

D. No idea, and nobody has checked

Reply with one letter — results next issue.

Nvidia shipped new open-weight models this week so agents can run inside a company or on a PC. What is the model family called?

Answer tomorrow — and no, we are not printing it here.

YESTERDAY'S ANSWER

Which benchmark or standard do enterprise compliance teams use most frequently to assess generative AI risk in financial services?

NIST AI Risk Management Framework (NIST AI RMF 1.0)

Want a look at where AI could save your team 5+ hours a week? Reply AUDIT — the desk takes a handful of these a month.