Compliance Services

Cyber Insurance
Penetration Testing

Meet your cyber insurance underwriting requirements with OSCP-certified penetration testing. Attestation letters, compliance-ready reports, and 5-day turnaround.

Why Cyber Insurance Carriers Require Penetration Testing

Insurance underwriters mandate security assessments to verify that your organization can defend against real-world threats.

Risk Mitigation

Underwriters need proof that your organization has conducted due diligence before issuing a cyber liability policy. Penetration testing demonstrates your commitment to security controls.

  • Validates existing security posture
  • Identifies exploitable vulnerabilities
  • Quantifies real-world risk exposure

Premium Discounts

Many insurers offer significant premium reductions for companies with documented penetration testing results. Your pentest investment often pays for itself in year-one savings.

  • 5-15% premium discount typical
  • ROI within first policy period
  • Competitive advantage in pricing

Underwriting Approval

Certain policy tiers and coverage limits require a signed attestation letter from a certified security professional confirming testing completion and key findings.

  • Attestation letter from OSCP professional
  • Executive summary for insurers
  • Accelerates policy approval

Timeline Compliance

Insurance renewals move fast. Our 5-day turnaround ensures your pentest report arrives before your underwriting deadline, not after.

  • 5-day turnaround guaranteed
  • No multi-month wait times
  • Meet renewal deadlines

What Insurance Underwriters Evaluate

Underwriters review pentest reports against a specific set of criteria. Our reports are built to satisfy them all.

Critical & High-Severity Vulnerabilities

Underwriters prioritize the number of critical and high-severity findings. Our reports clearly categorize and prioritize vulnerabilities by CVSS score and business impact, making it easy for insurers to assess your risk profile.

  • CVSS 3.1 scoring on all findings
  • Business impact justification
  • Realistic exploitability assessment
  • Clear severity categorization

Testing Methodology & Scope

Insurers want to know exactly what was tested. Our reports detail the scope, methodology, and testing dates so underwriters can verify appropriate coverage was assessed.

  • Detailed scope documentation
  • Methodology overview (PTES-aligned)
  • Testing date range
  • Systems and services tested

Remediation Guidance & Timeline

Underwriters appreciate actionable remediation steps. Our reports include prioritized remediation recommendations with estimated effort levels so you can demonstrate a clear path to improved security posture.

  • Remediation steps for each finding
  • Priority categorization (immediate, short-term, long-term)
  • Estimated remediation effort
  • References to security controls

Certifications & Professional Attestation

Insurers verify the tester's qualifications. All Trident Shell testing is conducted by Miguel, OSCP and CRTO certified. Your report arrives with a professional attestation letter confirming testing completion.

  • OSCP certification verification
  • Signed attestation letter
  • Professional credentials included
  • Tester background documentation

What You Get From Trident Shell

A complete package designed specifically to satisfy insurance underwriting requirements.

Comprehensive Report

100+ page professional assessment document with executive summary, technical findings, CVSS scoring, business impact analysis, and remediation roadmap.

Attestation Letter

Signed letter from OSCP-certified professional confirming testing completion, scope, methodology, and professional opinion on your security posture.

Insurer Summary

One-page executive summary specifically formatted for insurance underwriters, highlighting key metrics underwriters care about.

Consultation Call

Post-assessment call with Miguel to discuss findings, answer questions, and plan remediation steps forward.

Follow-Up Testing

Optional post-remediation verification testing to confirm fixes are effective and document progress for your insurer.

5-Day Turnaround

From assessment completion to report delivery in 5 business days or less, so you meet your insurance renewal deadlines.

Cyber Insurance Penetration Testing Process

From initial scoping to final attestation, we guide you through every step.

01

Scope & Planning

We discuss your insurance requirements, define testing scope, identify critical systems, and set expectations for insurer deliverables.

02

Security Assessment

Controlled penetration testing against your infrastructure and applications. We document all testing activities and findings in real-time.

03

Analysis & Classification

All vulnerabilities are analyzed, scored with CVSS metrics, and prioritized by business impact for your underwriter's review.

04

Report Generation

Professional assessment report written specifically for insurance underwriting, including attestation letter and executive summary.

05

Delivery & Consultation

Complete deliverables package delivered within 5 days, plus a consultation call to discuss findings and remediation roadmap.

Cyber Insurance Penetration Testing Pricing

Straightforward pricing designed to fit growing businesses. Results that often pay for themselves in premium reductions.

$2,500

Standard Cyber Insurance Penetration Test

  • External and internal network testing
  • Up to 5 critical systems/applications
  • 100+ page professional report
  • Attestation letter from OSCP-certified professional
  • Insurer summary document
  • 60-minute consultation call
  • 5-day turnaround guarantee

Typical ROI: Premium discounts of 5-15% usually offset the testing cost in the first policy year.

Timeline

  • Day 1: Assessment begins
  • Days 2-3: Testing execution
  • Days 4-5: Report finalization
  • Day 5: Delivery & consultation

Underwriter Requirements

  • OSCP or equivalent certification required
  • Testing methodology documentation
  • Professional attestation included
  • CVSS scoring for all findings

How Your Pentest Investment Pays for Itself

Most companies recover their testing costs within the first policy period through premium reductions.

Example: Mid-Market Technology Company

  • Annual cyber liability premium: $15,000
  • Typical discount with pentest: 10%
  • Annual savings: $1,500
  • Year 1 ROI on $2,500 test: 60% savings

Beyond the direct premium reduction, a pentest also strengthens your negotiating position for better coverage terms, higher limits, and more favorable exclusions. Companies that invest in documented security testing typically negotiate substantially better policies overall.

Common Questions About Cyber Insurance Testing

Everything you need to know before scheduling your assessment.

Do all cyber insurance carriers require penetration testing?

Most standard policies don't require it, but many underwriters offer 5-15% premium discounts when you provide testing results. Some higher-coverage-limit policies explicitly require it. Check with your broker — they often recommend it.

How do I choose what systems to test?

Focus on systems that handle sensitive data or support business operations. We'll help you prioritize based on your industry, data types, and insurance requirements. Most cyber insurance testing includes external network, internal network, and web application assessment.

Will the pentest disrupt my business?

We coordinate testing to minimize disruption. Most testing is non-destructive and happens during off-hours or maintenance windows when possible. We provide a detailed scope before we start so you can plan accordingly.

Can I use an old pentest for my insurance application?

Most underwriters prefer testing from the current calendar year or the previous 12 months. Older assessments are less valuable because your environment has likely changed. We recommend annual testing to keep your insurance optimized.

What if we find critical vulnerabilities?

That's why testing matters. We'll document everything clearly and provide remediation guidance. You can schedule follow-up testing after fixes to show your underwriter that vulnerabilities have been addressed. This actually strengthens your policy relationship.

Do I own the report?

Yes, the report is yours to share with your insurance broker and underwriter as needed. We provide it in a professional format suitable for insurance applications and policy renewals.

Schedule Your Cyber Insurance Penetration Test

Meet your insurance underwriting requirements with professional penetration testing. 5-day turnaround, attestation letter included, from $2,500.

OSCP Certified

Conducted by Miguel, OSCP and CRTO certified

5-Day Turnaround

Fast delivery for insurance deadlines

Maryland-Based

Local expertise, 24-hour response time

Contact Us for a Quote