What is Penetration Testing? A buyer’s Guide

Pennsylvania businesses—like their counterparts nationwide—face persistent cyber threats ranging from opportunistic hackers to sophisticated nation-state actors. The question isn't whether your organization will be targeted—but when. While vulnerability scans and security tools provide a baseline defense, they often leave critical gaps that only human-driven penetration testing can uncover.

What Is a Penetration Test?

A penetration test (often called a "pentest") is a controlled, authorized attempt to exploit vulnerabilities in your systems, networks, applications, or physical security measures. Unlike automated vulnerability scans, penetration tests involve skilled security professionals who think and act like real attackers—but with permission and clear boundaries.

Think of it this way: a vulnerability scan might tell you that your door is unlocked, but a penetration test shows what a motivated intruder could access once they're inside your building. For organizations in security-sensitive industries—whether in Philadelphia and the tri-state area or across the nation—this distinction is critical.

Why Organizations Need Penetration Testing

Three Primary Drivers

1. Cyber Insurance Requirements The cyber insurance market has hardened considerably, with carriers in the Northeast and across the country demanding rigorous security validation before issuing or renewing policies.

2. Regulatory Compliance Depending on your industry and location, you may face mandatory security testing requirements:

   • Healthcare: HIPAA requires regular security evaluations

   • Financial: PCI DSS explicitly requires penetration testing for cardholder environments

   • Critical infrastructure: Various sector-specific regulations mandate regular testing

   • State laws: A patchwork of regulations is emerging nationwide, from Maryland's Online Data Privacy Law (MODPL) and Pennsylvania's proposed Consumer Data Privacy Act (PCDPA) to California's Consumer Privacy Rights Act (CPRA), Virginia's Consumer Data Protection Act (VCDPA), and similar laws in Colorado, Utah, and Connecticut

   • Federal requirements: The Cybersecurity Maturity Model Certification (CMMC) framework is reshaping security requirements for defense contractors and their supply chains

   Organizations—from Philadelphia to Phoenix—are increasingly using penetration testing to validate their regulatory compliance and avoid potential penalties.

3. Third-Party Requirements As supply chain attacks increase, businesses are scrutinizing their vendors' security practices more closely than ever. If your company provides services or products to other organizations—particularly in the financial, healthcare, or government sectors—you've likely encountered security questionnaires asking specifically about penetration testing. Enterprises from Manhattan to Miami now require penetration test results before signing contracts with new vendors or partners, with particularly stringent requirements emerging in regulated industries and defense supply chains.

Beyond Compliance: Business Benefits

While regulatory compliance and third-party requirements often initiate the conversation, penetration testing delivers substantial business value beyond checking boxes:

• Prevent costly breaches: The average data breach in 2023 cost organizations $4.45 million—far more than the cost of proactive testing

• Validate security investments: Verify whether your security tools are actually working as intended

• Identify process failures: Discover where security policies are being ignored or circumvented

• Prioritize remediation efforts: Focus limited resources on fixing the most critical vulnerabilities first

• Build customer trust: Demonstrate commitment to security as a competitive advantage

The PTES Framework: Understanding the Penetration Testing Process

The Penetration Testing Execution Standard (PTES) provides a methodical approach to security testing that ensures consistency and comprehensive coverage. At Breach Craft, we follow this industry-standard framework for all assessments:

1. Pre-engagement Interactions: Defining scope, objectives, timelines, and constraints

2. Intelligence Gathering: Collecting information about the target environment

3. Threat Modeling: Identifying potential attack vectors and vulnerabilities

4. Vulnerability Analysis: Discovering weaknesses through scanning and manual testing

5. Exploitation: Safely attempting to leverage vulnerabilities to access systems

6. Post-Exploitation: Determining what an attacker could access after initial compromise

7. Reporting: Documenting findings, impact assessments, and remediation recommendations

This structured methodology ensures that testing is thorough rather than haphazard, aligned with business objectives rather than merely technical, and produces actionable results rather than overwhelming data dumps.

Types of Penetration Tests Your Organization May Need

Depending on your specific risk profile and industry, you might require different types of penetration testing:

• Network Penetration Testing: Assessing internal and external network security

• Web Application Testing: Evaluating customer-facing and internal web applications

• Cloud Security Assessments: Examining cloud infrastructure configuration and security

• API Testing: Verifying the security of application programming interfaces

• Physical Penetration Testing: Testing physical access controls and security measures

• Social Engineering: Evaluating human susceptibility to manipulation techniques

• Red Team Exercises: Comprehensive, objective-based security assessments

• Purple Team Exercises: Collaborative testing that combines offense and defense

A manufacturing business in eastern Pennsylvania might prioritize testing OT networks and physical security, while a financial services firm in Manhattan might focus on web applications and API security. Healthcare providers in New Jersey, tech startups in Austin, and government contractors in Virginia will each require a unique testing approach aligned with their specific risk profiles.

Choosing the Right Penetration Testing Provider

Not all penetration testing services are created equal. When evaluating potential providers, consider these critical factors:

Essential Criteria

1. Methodology and Approach

   • Do they follow a recognized framework like PTES?

   • Can they clearly articulate their testing process?

   • Do they customize testing based on your specific objectives?

2. Human Expertise vs. Automated Tools

   • Will actual security professionals be conducting the test?

   • What certifications do their testers hold (OSCP, GPEN, CISSP)?

   • How do they supplement tools with manual testing?

3. Reporting Quality

   • Ask for a sample report (with sensitive information redacted)

   • Is the report understandable to both technical and executive audiences?

   • Does it include clear remediation guidance?

4. Post-Assessment Support

   • Will they help explain findings to your technical team?

   • Do they offer remediation consultation or verification testing?

   • How accessible are they after delivering the report?

5. Regional Knowledge and Presence

   • Are they familiar with local regulatory requirements?

   • Do they understand your industry's specific challenges?

   • Can they provide references from similar organizations in your area?

Red Flags to Watch For

Beware of providers who:

• Offer penetration testing at unusually low prices

• Promise extremely rapid testing (1-2 days for complex environments)

• Can't differentiate between vulnerability scanning and penetration testing

• Won't provide sample reports or methodologies

• Lack documented processes for handling sensitive information

• Don't carry professional liability insurance

Organizations from Philadelphia to San Francisco have encountered "penetration testing" vendors who essentially run automated scans, add minimal analysis, and deliver reports that provide little actual security value. This problem plagues the industry nationally, making the distinction between genuine penetration testing and glorified scanning crucial when evaluating potential providers.

When and How Often to Conduct Penetration Tests

For most organizations, annual penetration testing represents the minimum prudent schedule. However, consider increasing frequency if your organization:

• Operates in a highly regulated industry

• Handles particularly sensitive data

• Makes frequent changes to infrastructure or applications

• Has experienced security incidents previously

• Faces unusually high threat levels

Timing penetration tests after significant infrastructure changes or application updates can also provide valuable validation before potential vulnerabilities affect your production environment.

Preparing for Your First Penetration Test

If your organization is planning its first penetration test, these steps will help ensure a productive engagement:

1. Define clear objectives beyond simply checking compliance boxes

2. Gather documentation on systems, networks, and applications

3. Notify relevant stakeholders without revealing specific testing times

4. Establish emergency contacts in case testing impacts operations

5. Create a remediation plan for addressing discovered vulnerabilities

6. Set appropriate expectations about findings and follow-up activities

The Bottom Line: Penetration Testing as Strategic Investment

Cybersecurity has evolved from a technical concern to a strategic business imperative. Whether you're operating in Philadelphia's finance sector, California's tech industry, or the manufacturing corridors of the Midwest, penetration testing represents not merely a compliance requirement but an essential investment in organizational resilience.

By proactively identifying and addressing security weaknesses before attackers can exploit them, your organization protects not only systems and data but also customer trust, brand reputation, and business continuity—assets that, once damaged, prove far more costly to rebuild than to protect.

Whether driven by regulatory requirements, cyber insurance demands, or third-party obligations, penetration testing delivers value that extends far beyond the immediate compliance benefit. In an environment where breaches regularly force companies out of business—particularly in the SMB sector from Pennsylvania to Oregon—security validation has become essential to survival.

Breach Craft provides expert penetration testing services to organizations throughout Philadelphia, Pennsylvania, New Jersey, Delaware, and across the United States. From our home base in Havertown, PA, our team of certified security professionals follows the PTES methodology to deliver thorough, objective-based testing that meets regulatory requirements while providing actionable security insights for businesses nationwide.