Cyber insurance proposals and AI leakage: what a cyber questionnaire gives away in ChatGPT or Claude.

A cyber questionnaire asks a client to describe, in its own words, every weakness in its systems. Brokers help complete it, and pasting the answers into ChatGPT or Claude is a tempting way to tidy the wording or check them against the insurer’s questions. The completed form says how many patient records the client holds, where they are backed up, who can log in remotely, how supplier payments are checked and what has already gone wrong. This page marks every item in a realistic dental practice proposal that the Insurance Contracts Act and the Privacy Act bear on, and shows how the same form is completed on Ermos inside the brokerage.

The cyber insurance questionnaire

Completed with the client before an insurer will quote cyber cover, and signed by a director with a declaration that the answers are true and complete.

An invented proposal. Hover or tap any highlighted item for the analysis; the full list is below.

What leaves the brokerage

1. 1
   The applicant, the address and the signatory

   The company, its trading name, the premises and the director who signed. Personal information about the director, and the identity of the business behind every answer below. Privacy Act guide.

2. 2
   Size and turnover

   Staff numbers and annual turnover. Confidential financial information, and the turnover figure also bears on whether the Privacy Act small business exemption applies to a business (a private sector health service provider is covered whatever its turnover). Privacy Act guide.

3. 3
   What personal information is held

   A count of patient records and the categories in them, including Medicare numbers and medical histories. It tells an attacker the value of the target and tells the insurer the scale of a possible breach. Health information is sensitive information under the Privacy Act. Patient data guide.

4. 4
   Where the data lives

   Which software, which server and an offshore cloud backup. A map of where to attack, and a disclosure question for the practice about patient data held overseas. Privacy Act guide.

5. 5
   The multi-factor authentication answers

   Which accounts have MFA and which do not, including a shared password for remote access. Published cyber proposal forms ask about MFA by service (email, remote access and privileged accounts). The answers are the practice’s weakest points in writing.

6. 6
   The backup weaknesses

   A restore test from 2023 and a cloud copy that syncs and can be overwritten. Forms commonly probe whether a backup is truly separate from the live system. These are the facts an attacker would most like to know.

7. 7
   The payment controls

   No call-back rule on supplier bank detail changes. Proposal forms commonly ask about a secondary check on changes of banking details, and the loss in the next item is what its absence looks like.

8. 8
   Past incidents and the open loss

   Two losses, one of them days old and uninsured, with a police report and a bank investigation. Proposal forms commonly ask about incidents in the past three years whether insured or not. Disclosure goes to the insurer under section 21 of the Insurance Contracts Act, which is not the same as telling an AI company.

9. 9
   The declaration wording

   The insurer’s standard declaration. It reflects the duty of disclosure in section 21 and the remedies in sections 28 and 60 of the Insurance Contracts Act, and it is the same text on every form of this kind, with no client data in it.

10. 10
    The broker’s note on the MFA attestation

    The broker’s advice not to sign an attestation that is not yet true, and that a director has not seen the answers. Advice the Code of Practice describes as honest and in the client’s best interests (clauses 3.1 and 5.3).

What happens in Frontier Models (ChatGPT, Claude)

• The whole document is transmitted to the provider’s servers. On personal plans the user cannot choose where it is stored or processed, and for the major providers that has generally meant outside Australia, under that country’s legal process. Some business plans offer storage in Australia, but the provider still receives the content.
• On consumer tiers, prompts can be retained and used to train future models.
• The provider’s staff and systems can reach the content under the provider’s own policies.
• Once sent, the brokerage no longer controls it. Retention and deletion happen on the provider’s terms.

The same document on Ermos

Part of AI data leakage in insurance brokerages.

Common questions