Penetration Testing Services

Penetration testing services simulate real-world attacks to uncover vulnerabilities across systems; Cherry Bekaert helps you identify risk and prioritize action.

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Threat Based Penetration Testing and Red Teaming Services for Middle-market Companies

Your security controls may look strong on paper. Penetration testing reveals whether they hold up when someone is actively trying to break through them.

Cherry Bekaert's penetration testing services simulate real-world attack scenarios across networks, applications, cloud environments and endpoints, exposing exploitable weaknesses before an adversary finds them. Findings are tied directly to business impact, giving security and technology leaders a prioritized, defensible roadmap for where to focus time, budget and resources to reduce risk. 

Benefits of Working With a Penetration Testing Firm 

Penetration testing exposes gaps, tells you whether your defenses work and gives you the evidence to act on it. Organizations that invest in penetration testing gain: 

  • Confirmed Visibility into Real Exploitable Weaknesses: Not theoretical risks, but validated findings an attacker could use today
  • Prioritized Business-impact: Remediation guidance ranked by consequence, so your team can address what matters most
  • Validation of Existing Security Controls: Confirmation that your investments in detection, response and prevention are performing as intended
  • Alignment Between Security Spending and Risk Reduction: Findings that connect directly to budget decisions and resource allocation
  • Audit and Compliance Support: Documented evidence of proactive security testing that satisfies requirements across frameworks, including NIST, PCI DSS, SOC 2 and HIPAA

Strengthen Your Security Posture With Confidence

Knowing your controls are effective and being able to demonstrate that to leadership, auditors and regulators is a competitive and operational advantage. Cherry Bekaert helps organizations assess real-world cyber risk, validate defenses and prioritize the actions that reduce exposure and support business performance.  

Penetration Testing Services

AI Red Teaming and Penetration Testing

Securing an AI system is not the same as securing the infrastructure it runs on. AI models, large language model (LLM) applications and autonomous agents introduce vulnerabilities that traditional penetration testing is not designed to find.

Cherry Bekaert's AI red teaming and penetration testing engagements evaluate how AI-enabled systems behave when someone is actively trying to manipulate, mislead or exploit them, testing for prompt injection and jailbreaking, data pipeline integrity, model access and API exposure, agentic system abuse, and safety control bypass. Findings are mapped to the OWASP Top 10 for LLM Applications, MITRE ATLAS and the NIST Generative AI Risk Management Framework, giving your security and compliance teams the documentation needed to drive remediation and support governance requirements. 

As AI becomes embedded in critical business operations, the question is no longer whether your models are deployed but whether they are deployed securely. 

External Penetration Testing

Your internet-facing assets are the first thing an attacker sees and are the most frequently targeted. Cherry Bekaert's external penetration testing identifies vulnerabilities in websites, portals and remote access points that could allow unauthorized entry, giving your team a prioritized view of exposure before an adversary can act on it. 

Internal Penetration Testing

The threat inside your perimeter is often more damaging than the one outside it. Cherry Bekaert's internal penetration testing advisors simulate an attacker who has already gained a foothold through compromised credentials, phishing or insider activity to determine how far they could move, what systems they could reach and how quickly sensitive data could be exposed. 

Network Penetration Testing

Knowing your network is configured correctly is not the same as knowing it will hold under attack. Cherry Bekaert's network penetration testing assesses internal and external infrastructure including servers, firewalls and endpoints to determine how far an attacker could move, what they could access and how quickly they could escalate privileges. Findings are mapped to business impact so your team knows exactly where to focus remediation. 

Web and Mobile Application Penetration Testing

Automated scanning tools find known vulnerabilities. They do not find how your application behaves when someone is actively trying to exploit it. Cherry Bekaert's application penetration testing evaluates web and mobile applications under real-world attack conditions uncovering flaws in business logic, APIs and user workflows that scanners miss and that attackers routinely exploit.  

Cloud Penetration Testing

Cloud environments expand your attack surface in ways traditional testing does not cover. Cherry Bekaert evaluates cloud infrastructure, configurations and access controls across platforms to identify misconfigurations, insecure APIs and privilege escalation paths that could expose sensitive data or disrupt operations. Testing covers both single-cloud and complex hybrid and multi-cloud environments. 

Social Engineering

Technology controls only go as far as the people operating them. Cherry Bekaert's social engineering simulations test how employees respond to phishing, pretexting and other manipulation tactics designed to bypass technical defenses, identifying gaps in awareness before a real attacker does and reinforcing the security behaviors that reduce human-layer risk across the organization. 

Threat-based Red Teaming

Standard penetration testing tells you where the gaps are. Threat-based red teaming tells you whether your people, processes and technology can detect and respond when a sophisticated adversary is actively working against you. Cherry Bekaert's engagements are built around threat intelligence relevant to your industry and operating environment, we simulate the tactics, techniques and procedures of realistic threat actors to stress-test your detection and response capabilities against the attacks most likely to target your organization.  

AI Red Teaming and Penetration Testing

Securing an AI system is not the same as securing the infrastructure it runs on. AI models, large language model (LLM) applications and autonomous agents introduce vulnerabilities that traditional penetration testing is not designed to find.

Cherry Bekaert's AI red teaming and penetration testing engagements evaluate how AI-enabled systems behave when someone is actively trying to manipulate, mislead or exploit them, testing for prompt injection and jailbreaking, data pipeline integrity, model access and API exposure, agentic system abuse, and safety control bypass. Findings are mapped to the OWASP Top 10 for LLM Applications, MITRE ATLAS and the NIST Generative AI Risk Management Framework, giving your security and compliance teams the documentation needed to drive remediation and support governance requirements. 

As AI becomes embedded in critical business operations, the question is no longer whether your models are deployed but whether they are deployed securely. 

External Penetration Testing

Your internet-facing assets are the first thing an attacker sees and are the most frequently targeted. Cherry Bekaert's external penetration testing identifies vulnerabilities in websites, portals and remote access points that could allow unauthorized entry, giving your team a prioritized view of exposure before an adversary can act on it. 

Internal Penetration Testing

The threat inside your perimeter is often more damaging than the one outside it. Cherry Bekaert's internal penetration testing advisors simulate an attacker who has already gained a foothold through compromised credentials, phishing or insider activity to determine how far they could move, what systems they could reach and how quickly sensitive data could be exposed. 

Network Penetration Testing

Knowing your network is configured correctly is not the same as knowing it will hold under attack. Cherry Bekaert's network penetration testing assesses internal and external infrastructure including servers, firewalls and endpoints to determine how far an attacker could move, what they could access and how quickly they could escalate privileges. Findings are mapped to business impact so your team knows exactly where to focus remediation. 

Web and Mobile Application Penetration Testing

Automated scanning tools find known vulnerabilities. They do not find how your application behaves when someone is actively trying to exploit it. Cherry Bekaert's application penetration testing evaluates web and mobile applications under real-world attack conditions uncovering flaws in business logic, APIs and user workflows that scanners miss and that attackers routinely exploit.  

Cloud Penetration Testing

Cloud environments expand your attack surface in ways traditional testing does not cover. Cherry Bekaert evaluates cloud infrastructure, configurations and access controls across platforms to identify misconfigurations, insecure APIs and privilege escalation paths that could expose sensitive data or disrupt operations. Testing covers both single-cloud and complex hybrid and multi-cloud environments. 

Social Engineering

Technology controls only go as far as the people operating them. Cherry Bekaert's social engineering simulations test how employees respond to phishing, pretexting and other manipulation tactics designed to bypass technical defenses, identifying gaps in awareness before a real attacker does and reinforcing the security behaviors that reduce human-layer risk across the organization. 

Threat-based Red Teaming

Standard penetration testing tells you where the gaps are. Threat-based red teaming tells you whether your people, processes and technology can detect and respond when a sophisticated adversary is actively working against you. Cherry Bekaert's engagements are built around threat intelligence relevant to your industry and operating environment, we simulate the tactics, techniques and procedures of realistic threat actors to stress-test your detection and response capabilities against the attacks most likely to target your organization.  

Our Professionals

Connect With Us

Kurt Manske headshot

Kurt Manske

Cybersecurity Leader

Partner, Cherry Bekaert Advisory LLC

Steven J. Ursillo, Jr. headshot

Steven J. Ursillo, Jr.

Cybersecurity

Partner, Cherry Bekaert LLP
Partner, Cherry Bekaert Advisory LLC

Penetration Test Services FAQs

Penetration testing requires documented authorization from system owners, clearly defining scope, timing and permitted activities. Organizations should establish rules of engagement, data handling requirements and incident protocols in advance. Testing should also align with regulatory requirements and contractual obligations to limit legal and compliance risk. 

Look for experience across relevant technologies, a structured methodology and clear reporting that prioritizes business risk. 

Common types include network, application, internal, external, wireless, cloud and social engineering testing. 

Most organizations conduct testing annually or after significant changes to systems, applications or infrastructure. 

A vulnerability assessment identifies and categorizes weaknesses, while penetration testing actively exploits them to demonstrate real-world impact. 

Penetration testing helps evaluate how vendor systems and integrations could introduce risk into your environment. It supports broader efforts by validating security controls

Contact Our Penetration Testing Services Team