5 Security Risks Your Cyber Insurance May Not Cover Without a Pen Test

Cyber insurance is a smart way to manage risk—but it’s not a get-out-of-jail-free card. In fact, many policies are full of exclusions and contingencies that could leave your business exposed if you haven’t taken reasonable steps to secure your environment. One of the most effective ways to demonstrate those steps? A penetration test.

Here are five common risks that your cyber insurance may not cover unless you’ve had a pen test or similar proactive security measure in place:

1. Outdated Software and Unpatched Systems

Insurance carriers often exclude claims resulting from unpatched vulnerabilities—especially those with available fixes. If a pen test had flagged that outdated Apache server or unpatched VPN, and it wasn’t addressed, your claim might be denied for “failure to maintain security standards.”

What a Pen Test Does: Identifies real-world exploitable vulnerabilities that scanners often miss or deprioritize.

2. Unauthorized Access from Weak Credentials

Default passwords, reused admin logins, or poorly secured remote access are favorite entry points for attackers—and an easy reason for insurers to deny a claim.

Why It Matters: Many cyber policies require you to prove that you implemented “industry standard” security practices. A pen test can help you find and fix these weak spots before an attacker—and your insurer—does.

3. Insecure Cloud or SaaS Configurations

Misconfigured cloud storage or user permissions in platforms like Microsoft 365 or AWS can lead to major breaches. Insurers often label this as “negligence” if you haven’t taken steps to secure them.

A Pen Test Helps You: Simulate an attacker’s view of your cloud environment and close the gaps before they become a legal and financial nightmare.

4. Third-Party Supply Chain Vulnerabilities

If a breach happens through a vendor or third-party integration, your insurer may only pay if you’ve assessed the risk beforehand.

Pen Tests Offer Insight: External scans and targeted tests can reveal insecure external assets or risky integrations you didn’t even know were there.

5. Policy Compliance Failures

Many cyber insurance policies require annual risk assessments, vulnerability scans, or penetration tests as part of the agreement. Skipping this step could mean you’re technically noncompliant—and ineligible for coverage.

Don’t Gamble on Loopholes: A pen test demonstrates due diligence and helps meet insurance policy requirements, compliance frameworks, and regulatory expectations.

Protect Your Business—and Your Policy

A penetration test isn’t just a best practice—it’s often the missing piece between a denied claim and a covered incident.

LightningSec offers autonomous penetration testing that’s fast, cost-effective, and run by real expert penetration testers. Whether you need to meet insurance requirements or just want peace of mind, we’re here to help.

Reach out today to schedule your autonomous pen test and lock in coverage confidence.