Hack Yourself First: Pen Testing for Prevention

August 19, 2025

By Mackenzie Gryder, with Ben Taylor

This blog is part of Gate 15’s Summer of Security: Ransomware Resilience Series, highlighting the essential considerations for organizational leaders and cybersecurity professionals.

Hack Yourself First: Pen Testing for Prevention.

This blog is part of Gate 15’s Summer of Security: Ransomware Resilience Series, highlighting the essential considerations for organizational leaders and cybersecurity professionals.

What are Penetration tests (pen-tests)?

Penetration tests (“pen tests”) are controlled, authorized attempts to break into an organization’s systems, networks, or applications just as a real attacker would. Unlike automated vulnerability scans, which identify known security flaws, pen-tests involve skilled testers using a combination of tools, tactics, and creativity to exploit weaknesses and demonstrate the potential impact of a breach. By proactively addressing these security gaps, organizations strengthen their defenses and reduce the likelihood of a successful ransomware breach.

Pen testers try to think like attackers, looking for overlooked misconfigurations, weak passwords, unpatched systems, insecure remote access, or other entry points that ransomware operators often target. They may attempt to gain initial access through phishing simulations, escalate privileges once inside, move laterally across your network, and identify critical systems or backups that could be targeted in a real ransomware attack.

There are different types of pen-testing, including:

External Testing: Targeting internet-facing assets such as websites, VPNs, or cloud services
Internal Testing: Assessing what an attacker could do once inside the network, whether through a phishing compromise or malicious insider scenario

Why Pen-Testing is Critical for Ransomware Defense:

Ransomware attacks often exploit easy entry points in an organization’s environment, including unpatched vulnerabilities, weak passwords, misconfigured backups, and open remote access. A regular pen-test helps you identify and fix these weaknesses before attackers can use them against you.

Penetration testing simulates how ransomware operators, testing your environment across the ransomware kill chain:

Initial Access: Can attackers breach your perimeter through phishing, stolen credentials, or exposed services?
Privilege Escalation: Can they elevate privileges to gain control of critical systems?
Lateral Movement: Can they move across your network to reach sensitive data or backups?
Data Access and Exfiltration: Can they reach, encrypt, or steal high-value data?

Benefits of Regular Pen-Testing:

Regular penetration testing offers organizations a proactive, measurable way to strengthen defenses against ransomware and other cyber threats.

Proactive Risk Reduction: Pen-testing helps uncover exploitable vulnerabilities before attackers find them, allowing organizations to fix issues and reduce the likelihood of a successful ransomware attack.
Informed Prioritization: Instead of patching everything blindly, pen-tests help you focus on the most critical weaknesses that could lead to real-world compromise, improving your patching and mitigation strategy.
Validation of Security Controls: Pen-tests test the effectiveness of your existing security layers, such as endpoint detection, backup protections, and segmentation, under realistic attack conditions.
Staff Training and Awareness: Pen-tests provide learning opportunities for your IT and security teams, showing how attacks unfold and where detection and response can improve.
Regulatory and Insurance Alignment: Many compliance frameworks recommend or require regular pen-testing as part of due diligence.
Continuous Improvement: Regular testing, combined with remediation, helps build a culture of security and continuous improvement, strengthening your overall cyber resilience posture.

How Often Should Organizations Perform Pen Tests?

The frequency of penetration testing depends on your organization’s size, industry, and risk profile, but regular testing is essential to stay ahead of evolving ransomware threats.

Some recommended guidelines include:

At least annually: Organizations should perform a comprehensive pen-test at least once a year to uncover new vulnerabilities and validate remediation efforts.
After major changes: Testing should be repeated after significant infrastructure or application updates, migrations, or policy changes to identify any new weaknesses.
High-risk environments: Critical infrastructure organizations may benefit from testing every 6 months or layering testing with continuous assessments.
Before compliance audits: Testing before compliance assessments helps identify and resolve issues proactively.

In addition to scheduled tests, combining regular pen-testing with continuous vulnerability scanning and security monitoring ensures you are not relying on a single snapshot in time to secure your environment.

Case Examples:

A case example comes from a UK Oil & Gas industry organization that was conducting routine monthly automated vulnerability scans. The scans were coming back clear, suggesting that all of their software was up to date. However, when conducting a manual penetration test, it was revealed that there was critical oversight where several remote management tools were installed with access to the same environment and had never been deleted. This allowed former employees to access sensitive company data. Identifying blind spots like this show why it is important to run a manual pen test on top of automated vulnerability scans as well as the importance of swift action to remediate critical issues.

Tips for an Effective Pen-Test Program:

Define Clear Objectives:
- Identify what you want to test.
- Align tests with your organization’s risk profile, compliance needs, and critical assets.
Scope Precisely:
- Set clear boundaries: what systems, IP ranges, and applications are in scope.Include third-party services if relevant and get necessary permissions.
- Incorporate threat intelligence and replicate threat actor TTPs which are known to target similar organizations.
Test Regularly:
- Perform at least annually or after significant changes.
- Consider periodic retests to verify that identified vulnerabilities are remediated.
Document Clearly:
- Provide a detailed report with findings, proof of concept, risk ratings, and clear remediation steps.
- Include an executive summary for leadership and technical details for IT teams.

Insights from our Weekly Ransomware Report.

Each week we publish our Weekly Ransomware Report (along with other all-hazards reports) through Gate 15’s Resilience and Intelligence Portal (GRIP). Contact us if you are interested in receiving the full report. Highlights from this week include:

Most Active Threat Actors (victim number): Safepay (5), Play (3)
Update: Data Leaked Palmgold Corporation Sdn. Bhd., Gambling Facilities and Casinos, Malaysai, First seen: 2025-08-18 15:23:01 UTC
Update: Data Leaked Adams Hearth & Home, LLC / Godby Hearth & Home, Retail, United States, First seen: 2025-08-15 18:46:48 UTC

Coming Up Next: “Patch It or Pay: Closing the Door on Exploits.” Unpatched systems are prime targets for ransomware. Timely patching ensures that known weaknesses are addressed, reducing the attack surface available to cybercriminals. By keeping systems up-to-date, organizations can prevent ransomware from taking advantage of unpatched vulnerabilities.

Gate 15 has worked across the Critical Infrastructure environment to develop cybersecurity plans and tabletop exercises for trade associations and owner/operators. We are pleased to offer 10% off ransomware exercises to new clients that are booked before 30 September 2025. Send out an email and mention this blog, and let’s discuss how to boost your organizational resilience together.

Join the GRIP! Stay informed of what’s new in all-hazards homeland security by joining the Gate 15’s Resilience and Intelligence Portal (GRIP). Join the GRIP! and join us in securing America’s people, places, data, and dollars. To join the GRIP, click the link above or here, scroll down and select the “Join the Grip!” button, or email our team at Gate15@Gate15.global.

Gate 15: Technology-enhanced, human-driven, homeland security risk management.