What is Penetration Testing? A Buyer's Guide

Pennsylvania organizations nationwide face ongoing cyber threats from opportunistic actors to sophisticated state-sponsored groups. While vulnerability scans and security tools offer baseline protection, they frequently miss critical gaps that only human-driven penetration testing can reveal.

What Is a Penetration Test?

A penetration test represents a controlled, authorized attempt to exploit vulnerabilities in your systems, networks, applications, or physical security measures. Unlike automated scanning, these assessments involve security experts who simulate real-world attack scenarios within agreed boundaries.

The distinction matters: vulnerability scans identify unlocked doors; penetration tests demonstrate what intruders could access inside.

Why Organizations Need Penetration Testing

Three Primary Drivers

1. Cyber Insurance Requirements Insurers increasingly demand rigorous security validation before issuing or renewing policies. A recent penetration test report often serves as evidence of due diligence.

2. Regulatory Compliance Industry-specific mandates drive testing requirements:

• Healthcare organizations must address HIPAA security requirements
• Financial services firms face PCI DSS mandates
• Critical infrastructure operators have sector-specific regulations
• State privacy laws (Pennsylvania PCDPA, California CPRA, Virginia VCDPA) impose data protection obligations
• Defense contractors must achieve CMMC certification

3. Third-Party Requirements Supply chain scrutiny has intensified, with enterprises requiring penetration test results before vendor partnerships. Your customers and partners want assurance that working with you won’t introduce risk to their operations.

Business Benefits Beyond Compliance

• Prevention of costly breaches (averaging $4.45 million in 2023)
• Validation of security tool effectiveness
• Identification of process failures and policy circumvention
• Prioritized remediation guidance based on actual exploitability
• Enhanced customer trust and competitive differentiation

The PTES Framework

The Penetration Testing Execution Standard (PTES) provides a methodical seven-step approach:

1. Pre-engagement Interactions - Defining scope, rules of engagement, and success criteria
2. Intelligence Gathering - Collecting information about targets through passive and active reconnaissance
3. Threat Modeling - Identifying likely attack vectors based on the target environment
4. Vulnerability Analysis - Discovering potential weaknesses in systems and applications
5. Exploitation - Attempting to leverage vulnerabilities to gain access
6. Post-Exploitation - Determining the value of compromised systems and maintaining access
7. Reporting - Documenting findings with technical details and business impact

Types of Penetration Tests

Network Penetration Testing

Evaluates your internal and external network infrastructure for vulnerabilities that could allow unauthorized access or lateral movement.

Web Application Testing

Focuses on custom applications, testing for OWASP Top 10 vulnerabilities, business logic flaws, and authentication weaknesses. Learn more about our application testing methodology.

Cloud Security Assessments

Reviews your AWS, Azure, or GCP configurations for misconfigurations, excessive permissions, and data exposure risks.

API Testing

Examines your application programming interfaces for authentication bypass, injection vulnerabilities, and data leakage. See our API security testing services.

Physical Penetration Testing

Tests physical security controls including access badges, locks, security guards, and surveillance systems.

Social Engineering

Evaluates your human security layer through phishing simulations, pretexting calls, and physical social engineering attempts.

Choosing the Right Provider

Essential Criteria

• Methodology adherence - Look for PTES or OSSTMM-based approaches
• Human expertise - Seek relevant certifications (OSCP, GPEN, CISSP) and demonstrated experience
• Quality reporting - Reports should serve both technical teams and executive audiences
• Post-assessment support - The best providers help you understand and remediate findings
• Regional knowledge - Familiarity with your industry and regulatory environment adds value

Red Flags to Avoid

• Unusually low pricing that suggests automated-only testing
• Rapid turnaround promises (1-2 days for comprehensive testing)
• Inability to differentiate scanning from actual penetration testing
• No sample reports or methodology documentation available
• Lack of professional liability insurance

Testing Frequency and Timing

Most organizations should conduct annual testing at minimum. Consider increasing frequency for:

• Highly regulated industries with sensitive data
• Organizations handling financial or healthcare information
• Environments with frequent infrastructure changes
• Companies that have experienced previous security incidents
• Businesses facing elevated threat levels

Preparing for Your Assessment

1. Define clear objectives beyond simply checking a compliance box
2. Gather system documentation including network diagrams and asset inventories
3. Notify stakeholders appropriately without compromising test integrity
4. Establish emergency contacts in case testing impacts production systems
5. Create remediation planning processes to act on findings quickly
6. Set realistic expectations for scope, timeline, and deliverables

Conclusion

Cybersecurity has evolved from a technical concern to a strategic business imperative. Penetration testing protects not just systems and data, but customer trust, brand reputation, and business continuity—assets far costlier to rebuild than to safeguard proactively.

Ready to assess your security posture? Contact Breach Craft for a consultation to discuss your penetration testing needs.