Compliance Services

Cyber Insurance
Penetration Testing

Your underwriter wants a pentest report. We deliver one they'll actually accept: OSCP-certified testing, signed attestation letter, and a report built for insurance review. Five business days, start to finish.

Why Your Insurer Wants a Pentest

Underwriters aren't asking for pentests because they think it's fun. They need to know you're not a liability waiting to happen.

Due Diligence

Before an insurer puts their money on the line, they want evidence that you've looked at your own security. A pentest is one of the clearest ways to show you've done that work.

  • Shows your current security posture
  • Finds vulnerabilities an attacker could use
  • Puts real numbers on your risk

Lower Premiums

Plenty of insurers knock 5-15% off your premium when you show up with pentest results. The testing often pays for itself in the first year just through that discount.

  • 5-15% premium reduction is typical
  • Usually recoups the testing cost in year one
  • Gives you leverage when shopping policies

Policy Approval

Some coverage tiers won't approve without a signed attestation letter from a certified tester. Not a vulnerability scan report. An actual pentest with a human behind it.

  • Signed attestation from an OSCP-certified tester
  • Executive summary written for insurers
  • Speeds up your approval process

Deadline Friendly

Renewal dates don't move. We turn around reports in 5 business days so you're not scrambling to get documentation to your broker at the last minute.

  • 5-day report turnaround
  • No months-long queues
  • Built for renewal timelines

What Underwriters Actually Look At

We've seen enough underwriter checklists to know what they're scanning for. Our reports are built to check those boxes.

Critical & High Findings

The first thing an underwriter does is look at how many criticals and highs you have. We score every finding with CVSS 3.1 and explain the actual business impact, not just a scanner output number.

  • CVSS 3.1 scoring on every finding
  • Business impact explanation in plain language
  • Honest exploitability assessment
  • Clean severity breakdown

Scope and Methodology

Insurers want to confirm the test actually covered the right stuff. Our reports spell out what was tested, how it was tested, and when. No ambiguity.

  • Full scope documentation
  • PTES-aligned methodology
  • Exact testing dates
  • Complete list of systems and services tested

Remediation Plan

Underwriters like seeing that you know what to fix and how. Each finding comes with specific remediation steps and a rough effort estimate so you can show a plan, not just a list of problems.

  • Fix steps for every finding
  • Prioritized: immediate, short-term, long-term
  • Effort estimates included
  • Mapped to relevant security controls

Tester Credentials

Insurers check who did the testing. All testing is performed by Miguel Velazco, OSCP and CRTO certified. Your report includes a signed attestation letter confirming the work was completed.

  • OSCP and CRTO certifications
  • Signed attestation letter
  • Tester credentials documented
  • Professional background included

What's in the Box

Everything your broker needs to hand off to the underwriter.

Full Report

The main document. Executive summary, technical findings, CVSS scores, business impact, and a remediation roadmap. Typically 100+ pages depending on scope.

Attestation Letter

Signed letter confirming what was tested, how, and by whom. This is the document most underwriters specifically ask for.

Insurer Summary

A one-pager formatted for underwriters. Hits the key metrics they care about without burying them in technical detail.

Debrief Call

A call with Miguel after delivery to walk through findings, answer questions, and talk through what to fix first.

Retest (Optional)

After you've fixed things, we can verify the fixes and document the improvement for your insurer.

5-Day Turnaround

Assessment to report delivery in 5 business days. You won't miss your renewal deadline.

The Process

Straightforward. No surprises.

01

Scoping Call

We talk through your insurance requirements, figure out what systems need testing, and agree on scope. If your broker sent you specific requirements, bring those to the call.

02

Testing

Hands-on penetration testing against your infrastructure and applications. Everything gets documented as we go.

03

Analysis

Findings are scored, validated, and prioritized by actual business impact. No inflated severity counts.

04

Reporting

The full report, attestation letter, and insurer summary get written up and quality-checked.

05

Delivery

You get everything within 5 days, plus a debrief call to go over what we found and what to prioritize.

Cyber Insurance Penetration Testing

Scoped to your environment. No fixed tiers. The testing cost usually pays for itself in premium savings.

Cyber Insurance Penetration Test

Custom-scoped to your policy requirements

  • 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 debrief call
  • 5-day turnaround guarantee
Request a Custom Proposal

Typical ROI: Most clients see a 5-15% premium discount that offsets the testing cost within the first policy year.

Timeline

  • Day 1: Assessment kicks off
  • Days 2-3: Active testing
  • Days 4-5: Report writing
  • Day 5: Delivery + debrief call

What Underwriters Expect

  • OSCP or equivalent certification on the tester
  • Documented testing methodology
  • Signed professional attestation
  • CVSS scoring on all findings

The Math Usually Works Out

Most companies recover the testing cost through premium reductions in year one.

Example: Mid-Size Tech Company

  • Annual cyber liability premium: $15,000
  • Typical pentest discount: 10%
  • Annual savings: $1,500
  • Year 1: testing cost largely offset by savings

The premium discount is just part of it. Having a pentest on file also gives you a stronger position when negotiating coverage terms, higher limits, and better exclusions. Insurers treat tested companies differently than untested ones.

Common Questions

What people usually ask before booking.

Do all cyber insurance carriers require a pentest?

Most standard policies don't explicitly require it, but a lot of underwriters offer 5-15% premium discounts if you have one. Higher coverage limits often do require it. Talk to your broker. They'll tell you if it's mandatory or just strongly recommended.

How do I figure out what to test?

Start with whatever touches sensitive data or keeps the business running. We'll help you narrow it down during the scoping call based on your industry and your insurer's requirements. Most insurance pentests cover external network, internal network, and web apps.

Will this break anything?

We test carefully. Most of what we do is non-destructive, and we coordinate timing with your team. You'll see the full scope before we start so there are no surprises.

Can I use last year's pentest?

Most underwriters want something from the last 12 months. Your environment changes, so older reports don't carry much weight. Annual testing is the safest bet for keeping your policy in good shape.

What if you find something bad?

Good. That's the point. We document everything and tell you exactly how to fix it. You can do a follow-up retest after remediation to show your underwriter the problems are gone. Insurers actually like seeing that cycle.

Do I own the report?

Yes. It's yours. Share it with your broker, your underwriter, whoever needs it. We format it so it's ready for insurance submissions and renewals.

Get Your Insurance Pentest Scheduled

Attestation letter, insurer-ready report, 5-day turnaround. Scoped to what your policy actually requires.

OSCP Certified

Testing done by Miguel, OSCP and CRTO certified

5-Day Turnaround

Won't miss your renewal deadline

Maryland-Based

Local firm, 24-hour response time

Contact Us for a Quote