Cyber insurers have tightened underwriting significantly in recent years, and many policies now condition coverage, or a favourable premium, on documented evidence of security controls — including recent, independent penetration testing. A vague answer on an underwriting questionnaire is increasingly a reason for a higher premium, a coverage exclusion, or a declined claim.
We deliver testing evidence structured for exactly what underwriters and brokers ask to see.
We scope testing to your externally facing systems and the infrastructure most underwriting questionnaires ask about directly — remote access, backup isolation, privileged access controls — and report findings in a format your broker can attach to a renewal or new-policy submission without rework.
Why it matters
Ransomware claims have driven insurers to underwrite far more carefully than a few years ago, and ambiguous or unverified answers on a security questionnaire routinely translate into higher premiums or coverage limitations. Independent penetration test evidence is one of the clearest ways to demonstrate the controls insurers are specifically pricing risk against.
What we test
- External perimeter & attack surface penetration testing
- Remote access & VPN security testing
- Backup isolation & immutability validation
- Privileged account & MFA implementation testing
- Ransomware attack-path simulation
- Underwriting-questionnaire evidence pack preparation
Common vulnerabilities we uncover
- Exposed remote access without multi-factor authentication
- Backups reachable and destroyable from the production network
- Flat networks enabling fast ransomware lateral movement
- Privileged accounts without adequate MFA or monitoring
- No recent, independent testing evidence for underwriting
- Answers on the insurance questionnaire that do not match technical reality
Our methodology
- Scoping & rules of engagement. We agree objectives, targets and boundaries for your cyber insurance penetration testing, so testing is safe, authorized and focused on what matters to your business.
- Reconnaissance & mapping. We enumerate the full attack surface in scope, building a complete picture before any exploitation begins.
- Manual exploitation. Our senior testers chain vulnerabilities by hand — going far beyond automated scanners — to prove real, demonstrable impact.
- Analysis & reporting. Every finding is triaged, risk-rated with CVSS and written up with a copy-paste reproduction and clear remediation.
- Remediation support & free retest. We support your team through the fixes and retest the remediated issues to confirm they are genuinely closed.
Tools & techniques
We test the systems and controls cyber insurance underwriting questionnaires most commonly ask about — external perimeter exposure, remote access and VPN security, backup isolation and immutability, privileged account controls and multi-factor authentication — and write findings so your broker can present them directly to an underwriter.
When you need this engagement
- You are renewing a cyber insurance policy and want a stronger underwriting position
- A broker or insurer has requested evidence of penetration testing
- Your last policy renewal came with a higher premium citing security gaps
- You are securing cyber coverage for the first time
- You want confidence a claim would not be challenged over unverified security answers
What you receive
- Penetration test report scoped to underwriting-relevant systems
- Ransomware attack-path findings
- Backup isolation & MFA validation results
- Underwriting-questionnaire evidence pack
- Prioritised remediation roadmap
- Free retest after remediation
What’s included in your report
Every cyber insurance penetration testing engagement concludes with a comprehensive, board-ready report and a working session to walk your team through it. Your report includes:
- An executive summary with overall risk posture for non-technical stakeholders
- Detailed technical findings, each with a step-by-step, copy-paste reproduction
- CVSS v3.1 severity ratings and business-impact context for every issue
- Prioritized, actionable remediation guidance your engineers can apply directly
- A complimentary retest to confirm fixes and update finding status
- A formal attestation letter for customers, auditors and compliance programs
Standards & frameworks
NIST Cybersecurity Framework (underwriting alignment)
MITRE ATT&CK
Outcomes you can expect
After your cyber insurance penetration testing, you will have clear, evidence-based visibility into your real security risk — not a scanner’s guesswork. You will know exactly which weaknesses an attacker could exploit, what the business impact would be, and the precise steps to fix them in priority order. Teams use our findings to close critical gaps, satisfy customer and regulator security requirements, and demonstrate due diligence to their board. With a complimentary retest included, you also get documented proof that the issues are genuinely resolved.
Engagement details & logistics
Every cyber insurance penetration testing starts with a short, no-obligation scoping call to understand your goals, environment and constraints, followed by a fixed-price proposal and a clear statement of work. Most engagements are delivered fully remotely, with on-site work arranged where it genuinely adds value. Throughout testing we maintain an agreed communication cadence and escalate any critical, high-impact finding to you immediately rather than waiting for the final report. All work is performed under a signed NDA with strict data-handling controls, using safe, non-disruptive techniques and carefully coordinated rules of engagement to protect your production systems. On completion you receive your report and a walkthrough session, followed by a complimentary retest once your fixes are in place. Typical engagements are booked one to three weeks in advance, and urgent or pre-deadline testing can often be accommodated — just ask at hi@agentoffense.com.
Why organizations choose AgentOffense
Our cyber insurance penetration testing is delivered by senior offensive-security engineers who test the way real attackers do — manually, creatively and with a relentless focus on proving genuine, demonstrable impact. Here is what sets our engagements apart:
- Manual, exploit-driven testing that chains vulnerabilities the way a real attacker would, going far beyond what automated scanners can find.
- Reproducible proof for every finding, with copy-paste reproduction steps your engineers can follow and independently verify.
- Honest severity calibration so you invest in fixing what genuinely matters and avoid wasting effort on false positives and noise.
- Clear, business-focused reporting that speaks to engineers and executives alike, tying every issue to real-world impact.
- A complimentary retest included, so you get documented proof that your fixes actually close the attack path.
- Responsible, collaborative delivery with a named point of contact and secure handling of all data throughout the engagement.
Explore related services
Cyber Insurance Penetration Testing is frequently scoped alongside our other offensive-security services for broader coverage. Explore related engagements that complement it:
- Ransomware Readiness Assessment — Ransomware readiness assessment — attack-path simulation, backup and recovery validation, and detection testing against real ransomware…
- External Network Penetration Testing — External network penetration testing of your internet-facing perimeter — exposed services, misconfigurations and exploitable hosts, tested…
- Internal Network Penetration Testing — Internal network penetration testing — lateral movement, privilege escalation and segmentation review from an assumed-breach position…
How much does Cyber Insurance Penetration Testing cost?
Every cyber insurance penetration testing is scoped and priced individually, so you pay for exactly the coverage you need — with no hidden extras. After a short, no-obligation scoping call we send a fixed-price quote, usually within one business day, with clear deliverables, a firm timeline and a complimentary retest included. The price of your cyber insurance penetration testing depends on the size and complexity of the target and the depth of testing required, so you always know the cost up front before any work begins.
Get a fixed-price quote
Frequently asked questions
Do insurers actually require penetration testing?
Not universally by name, but most underwriting questionnaires ask detailed questions a penetration test directly answers, and providing independent evidence rather than self-reported answers increasingly affects both premium and coverage terms.
What do underwriters care about most?
In practice: multi-factor authentication on remote access and privileged accounts, backup isolation from production, and evidence you can detect and contain ransomware-style lateral movement — we weight testing accordingly.
Can this help lower our premium?
We cannot guarantee pricing outcomes, but documented, independent evidence addressing the controls underwriters price against is one of the clearest levers policyholders have in renewal negotiations.
How often should we test for insurance purposes?
Annually at minimum, timed ahead of your renewal date so findings can be remediated and evidenced before you submit.