AI Assistant Oversharing
One ordinary question. Fourteen colleagues' salaries in the answer.
What Is AI Assistant Oversharing?
A company assistant searches everything your account can open, not only what you were meant to see. A file nobody could find by browsing becomes one question away the day the assistant is switched on. In this exercise a routine budget question comes back with fourteen colleagues' salaries, cited from a payroll file shared with the whole company by mistake. You practise reading the source chips, checking the file's access panel, reporting the share instead of using the answer, and giving your manager the figure from the approved budget.
What You'll Learn in AI Assistant Oversharing
- Recognise that a company AI assistant reads with your own permissions, so an answer can only contain what your account could already open
- Treat unexpected access as a signal: an answer containing data you have no business reason to see means a file is over-shared, not that the assistant misbehaved
- Use an assistant's cited sources to find where an answer came from and who else can see that file
- Check a file's access list in the file manager to read the sharing history, including who shared it, when, and why
- Report an over-shared file to IT Security and its owner rather than using, forwarding or deleting it, and answer the original question from the approved source
AI Assistant Oversharing — Training Steps
-
Budget Week
It is Tuesday, 13:40. Tavenholm Packaging switched on Tavenholm Ask three weeks ago, a company assistant wired into mail, the shared drive and WorkStream, so nobody has to dig for a file again. You are pulling numbers together for David Park's Q4 plan, and the deadline is this afternoon.
-
David Needs A Number
David Park messages you directly. He is building the Q4 plan and wants one figure he does not have yet.
-
Open Tavenholm Ask
Tavenholm Ask lives in the browser. It shows what it is connected to before you type anything: your mailbox, the shared drive, and the chat channels you are in.
-
Ask The Question
Ask David's question the way he phrased it. There is nothing unusual about it, which is the point.
-
Ask Writes The Answer
Tavenholm Ask searches, then writes. Watch what it puts on the screen.
-
Read What It Found
The answer is correct, well organised and four seconds old. It also contains something David never asked for and you were never meant to see.
-
Did It Break In
Before you look any closer, settle how this happened.
-
Open The Source
Under the answer, Tavenholm Ask lists what it read. The first chip is the payroll file. Click it and the assistant tells you where the file lives and who can see it.
-
Check It In Files
The assistant's summary of the sharing is one line. The file itself keeps the whole story: who shared it, when, and why. That lives in the Files app, under Who has access.
-
Who Can See It
The access panel lists every principal on the file. Two of the three are exactly what you would expect. The third is the problem, and the note beside it explains how it got there.
Security Framework Coverage
OWASP LLM Top 10
- LLM02:2026 Sensitive Information Disclosure
CIS Controls
- CIS 14.4 Train Workforce on Data Handling Best Practices
- CIS 3 Data Protection
NIST CSF
- PR.AT-01 Personnel are provided with awareness and training so that they possess the knowledge and skills to perform general tasks with cybersecurity risks in mind
- PR.DS Data Security
GDPR
- Art. 5 Principles relating to processing of personal data (integrity and confidentiality)
- Art. 32 Security of processing
EU AI Act
- Art. 4 AI literacy