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Automated Penetration Testing

What Is Penetration Testing?

Penetration testing is a structured security assessment that actively attempts to exploit vulnerabilities in your environment, the way a real attacker would. Where vulnerability scanning identifies potential weaknesses, penetration testing goes further: it validates which vulnerabilities are actually exploitable, how far an attacker could get, and what the real business impact would be.

Automated penetration testing combines the breadth of automated tooling with prioritized, expert-reviewed findings to deliver a comprehensive picture of your security posture. The result is a report your team can act on: not just a list of things that might be wrong, but a clear view of what can actually be exploited and what to fix first.

Vulnerability Scan vs. Penetration Test

Vulnerability scanning and penetration testing are often confused. A vulnerability scan identifies systems and software with known weaknesses. It tells you what might be exploitable. A penetration test actively attempts to exploit those weaknesses, chains multiple vulnerabilities together to simulate a realistic attack path, and shows you what an attacker could actually access.

Both have value, but they answer different questions. A scan tells you what might be wrong. A penetration test tells you what's actually dangerous. Compliance frameworks, cyber insurers, and enterprise customers are increasingly asking for the latter.

Need reliable IT support for your business? Reach out to learn how STACK Cybersecurity can support your IT and cybersecurity.

What Gets Tested

Penetration testing scope is defined based on your environment and objectives. Common test types can be scoped individually or combined for broader coverage.

External Network

External Network

Testing of internet-facing systems, services, and infrastructure to identify exploitable entry points an attacker could use to gain initial access to your environment.

Internal Network

Internal Network

Simulation of an attacker who has already gained access, testing lateral movement, privilege escalation, and the ability to reach sensitive systems and data from inside the network.

Cloud and SaaS

Cloud and SaaS

Assessment of cloud environment configurations, IAM policies, storage permissions, and exposed APIs to identify misconfigurations that could allow unauthorized access or data exposure.

Credential and Identity

Credential and Identity

Testing of authentication controls, password policies, MFA enforcement gaps, and privilege escalation paths that could allow an attacker to move from a standard account to elevated access.

Vulnerability Chaining

Vulnerability Chaining

Identification of attack paths that combine multiple lower-severity vulnerabilities into a higher-impact exploit chain, revealing risks that individual vulnerability scans would miss.

Compliance Testing

Compliance Testing

Scoped testing aligned to specific framework requirements, including PCI DSS, HIPAA, SOC 2, and CMMC, with findings mapped to relevant controls for audit documentation.

Penetration Testing Report and Remediation

What You Get

A penetration test is only as valuable as the report that comes out of it. A list of CVEs with severity scores isn't actionable. STACK delivers findings that are validated, prioritized by real-world exploitability, and explained in terms your team can act on.

The report includes an executive summary for leadership, a technical findings section with proof of exploitation and remediation steps, prioritized recommendations ordered by risk impact, and compliance mapping where applicable. After remediation, retesting confirms that identified issues have been closed.

Compliance and Cyber Insurance Requirements

Annual penetration testing is required or strongly recommended by most major compliance frameworks. PCI DSS requires annual penetration testing for payment data environments. SOC 2 auditors expect penetration test results as evidence of security program effectiveness. HIPAA guidance recommends regular testing of technical safeguards. CMMC assessors expect evidence that security controls have been validated through testing, not just documented.

Cyber insurers are increasingly requiring annual penetration test results as a condition of coverage or to qualify for preferred rates. Having a current test report on file demonstrates that your security program is active, not just documented.

Ready to See What an Attacker Would Find?

Most businesses are surprised by what a penetration test uncovers. Knowing your real exposure is the first step toward fixing it. STACK can scope an engagement appropriate for your environment and deliver findings your team can act on before your next compliance cycle or insurance renewal.

Cybersecurity Consultation

Do you know if your company is secure against cyber threats? Do you have the right security policies, tools, and practices in place to protect your data, reputation, and productivity? If you're not sure, it's time for a cybersecurity risk assessment (CSRA). STACK Cybersecurity's CSRA will meticulously identify and evaluate vulnerabilities and risks within your IT environment. We'll assess your network, systems, applications, and devices, and provide you a detailed report and action plan to improve your security posture. Don't wait until it's too late.

Schedule a Consultation Explore our Risk Assessment