How do I answer the cyber insurance questions about penetration testing and security assessments?
The forms ask whether you have a penetration test or a security assessment each year, and whether an outside firm does it.
Last read from the sources at the foot of this page.
What exactly does the form ask?
These are the forms' own words, with the form and page each comes from.
Annual penetration testing
Annual network security assessments
If Yes, are such assessments conducted by a third party service provider?
How often do you conduct penetration testing of your network architecture?
What does it mean for a small firm?
A penetration test is an authorised attempt to break in. A security assessment is a review of how exposed you are. The forms ask about them separately.
How do I answer it truthfully?
Answer the penetration test question with tests that tried to break in. If you had an outside assessment, give its date and who did it under the assessment question, and ask your broker which question the insurer counts it under.
What can an outside reading show, and what can it not?
An outside reading attacks nothing and tries no password. It reads what your domain shows anyone, so it is not a penetration test and should not be called one.
It cannot see inside your network.
Where does this come from?
- Travelers, CyberRisk Application (CYB-14102 Ed. 01-19)travelers.comRead 14 October 2026
- Victor Insurance Managers, Cyber insurance application (Sept. 8/23)victorinsurance.caRead 14 October 2026
See what is open before anyone else does.
We read from outside, find each way in first, and show it with a check anyone can re-run. No access, nothing tested, no obligation.
- We read your firm from outside.
- You see what is open, with the proof for the lead finding.
- If it is worth it, you order.
What happens if you go ahead. More at getleaktrace.com/see-it-first/.
Read the transcript
- 72 hours. One domain. Nothing to install.
- Discover. Every way in, found from outside.
- Validate. Every finding, proven. Dated and checkable by anyone.
- Close. Forged email: one click per step, where we reach your DNS host and you approve it.
- You get the fix for the rest, step by step, and we re-check until it is closed.
- Monitor. On monitoring: email settings, look-alikes and new host names re-checked every hour. Alerts within the hour.
- Every paid assessment is human-verified before release.
- The AI defense layer for businesses. getleaktrace.com/see-it-first/