Penetration Testing

A controlled, authorized simulation of a real-world cyberattack against your systems. We don't just scan for weaknesses. We exploit them, safely, to show you exactly what an attacker could achieve and how to stop them.

What Is Penetration Testing?

Penetration testing is a hands-on, authorized attack simulation performed by our security professionals against your systems, networks, and applications. Unlike automated scanning, a penetration test involves real people using real attacker techniques to find and exploit vulnerabilities, demonstrating exactly what a malicious actor could accomplish if they targeted your organization.

The difference between a vulnerability scan and a penetration test is the difference between knowing a door might be unlocked and actually walking through it. We safely exploit weaknesses to demonstrate real impact: stolen data, compromised accounts, lateral movement across your network, and escalation to critical systems. Then we show you exactly how to lock it all down.

68%

Of organizations have never had a penetration test performed on their systems. They're relying on automated scans and assumptions. That means most businesses have no idea what an actual attacker could do once they get past the perimeter.

$4.9M

Is the average total cost of a data breach in 2025. That figure includes incident response, legal fees, regulatory fines, lost business, and reputational damage. A penetration test costs a fraction of that and shows you where the breach would happen before it does.

"A penetration test doesn't just tell you what's vulnerable. It shows you what happens when those vulnerabilities are chained together by someone who knows what they're doing."

Types of Penetration Tests

Grey Team Foundation offers multiple penetration testing approaches depending on what you need to learn about your security posture. Each approach simulates a different type of adversary and provides different insights into your defenses.

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External Network Penetration Test. We attack your organization from the outside, just like a real adversary would. Starting with only your company name or a list of external IP addresses, we attempt to breach your perimeter defenses, compromise internet-facing systems, and gain access to your internal network.
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Internal Network Penetration Test. Simulates an attacker who has already gained a foothold inside your network, whether through a compromised employee account, a phishing attack, or physical access. We test internal segmentation, privilege escalation paths, and how far an attacker can move laterally once inside.
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Web Application Penetration Test. A hands-on assessment of your web applications targeting the OWASP Top 10 and beyond. We test for injection flaws, authentication bypass, session management issues, and business logic vulnerabilities that automated scanners typically miss.
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API Penetration Test. If your systems rely on APIs for internal communication or customer-facing services, we test them for authentication weaknesses, data exposure, injection vulnerabilities, and access control bypass that could allow unauthorized access to sensitive data or functionality.
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Mobile Application Penetration Test. We assess your iOS and Android applications for insecure data storage, weak transport security, improper session handling, and backend API vulnerabilities. Each platform is tested independently because each has its own unique attack surface.

Testing Approaches

We tailor the level of information provided to our testers based on what you want to learn:

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Black Box. Our testers receive no prior knowledge of your environment. This provides the most realistic simulation of an external attacker and tests your perimeter defenses, detection capabilities, and incident response readiness.
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Grey Box. Our testers receive limited information such as standard user credentials, simulating a compromised employee or malicious insider. This is highly effective for testing internal segmentation, access controls, and privilege escalation paths.
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White Box. Our testers receive full access to documentation, configurations, and source code. This removes the discovery phase entirely, allowing for the most thorough and comprehensive assessment possible, uncovering deep flaws that black or grey box testing might miss.

How the Engagement Works

Every penetration test follows a controlled, methodical process. We operate under strict rules of engagement defined with your team before any testing begins, ensuring safety, legal compliance, and minimal disruption to your operations.

Rules of Engagement and Scoping

We define the engagement scope, testing approach, target systems, exclusions, testing windows, and emergency contacts. A formal authorization document is signed before any testing begins. This protects both parties and ensures everyone is aligned on objectives and boundaries.

Reconnaissance and Discovery

Depending on the testing approach, we gather information about your environment using the same techniques real attackers use. For black box engagements, this means starting from scratch. For grey and white box tests, we leverage the information provided to focus on deeper, more targeted testing.

Exploitation and Attack Simulation

This is where the test gets real. We attempt to exploit identified vulnerabilities, chain them together, escalate privileges, move laterally through your network, and access sensitive data. Every action is logged and documented. We follow the principle of minimal harm: proving access without causing damage.

Post-Exploitation and Impact Analysis

When we gain access, we document exactly what we could reach, what data was exposed, and what level of control we achieved. This demonstrates real-world business impact, not just theoretical risk scores, but concrete proof of what an attacker could do to your organization.

Reporting and Debrief

You receive two deliverables: an executive summary for leadership explaining what was compromised and what it means for the business, and a detailed technical report with attack chains, evidence screenshots, CVSS scores, and step-by-step remediation guidance. We also conduct a live debrief with your team to walk through every finding and answer questions.

Why This Matters for Your Business

Penetration Testing is the fourth module in the C.V.I.P²-A framework because it builds on everything that comes before it. The Cyber Threat Surface Overview maps your exposure. The Vulnerability Assessment identifies your weaknesses. Intelligence Collection reveals what attackers already know about you. Penetration Testing puts all of that to the test by simulating what happens when a skilled adversary puts it all together.

For Medium and Large organizations, Grey Team requires a Vulnerability Assessment before any penetration test. This ensures that basic, known issues are already identified so the penetration test can focus on advanced attack paths, chained exploits, and complex scenarios that automated scanning would never catch. For Small businesses, we offer more flexibility, but we always recommend the assessment-first approach.

Penetration testing is required or strongly recommended by virtually every major compliance framework, including PCI DSS v4.0, HIPAA, NIST CSF 2.0, NYDFS 23 NYCRR 500, SOC 2, and ISO 27001. If your organization is subject to any of these standards, regular penetration testing isn't optional.

Who Should Get This Assessment

Any organization that wants to know, with certainty, whether their defenses would hold up against a real attack. This is especially critical for:

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Healthcare organizations. HIPAA requires regular security testing, and patient data is among the most targeted on the dark web. A penetration test reveals whether your EHR systems, patient portals, and connected devices could be compromised by a determined attacker.
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Restaurants, retail, and hospitality. PCI DSS v4.0 requires annual penetration testing for merchants processing card payments. If an attacker can reach your POS systems or payment processing environment, you need to know before they do.
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Banks, credit unions, and financial services. Regulatory bodies expect regular penetration testing as evidence of a mature security program. The stakes are high: a successful breach in financial services triggers mandatory reporting, regulatory scrutiny, and significant financial penalties.
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Law firms and professional services. A compromised law firm doesn't just lose its own data. It loses its clients' data, including privileged communications, case strategy, and financial records. Penetration testing validates that your security controls actually protect what matters most.
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Manufacturing and supply chain. Operational technology environments are increasingly connected to IT networks, and attackers know it. A penetration test can reveal whether an attacker could pivot from a compromised workstation into production systems that control physical processes.

Test Your Defenses Before They Do

Complete the form and a Grey Team Foundation security advisor will discuss scoping a penetration test for your environment.

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