Penetration testing, often referred to as ethical hacking, is a controlled and authorized simulation of real-world cyberattacks to identify security weaknesses before adversaries can exploit them.
Different penetration testing methodologies target distinct layers of your environment, including internal and external networks, web applications, cloud services, wireless systems, and physical facilities. Choosing the right method depends on your organization’s risk profile, infrastructure, and compliance requirements.
To ensure comprehensive coverage, many businesses conduct multiple types of tests throughout the year, often following frameworks like the OWASP Penetration Testing Methodologies, or NIST 800-115 (Technical Guide to Security Testing), among others commonly used across the industry.
Network penetration testing focuses on assessing the security posture of internal, external, and wireless networks. Testers identify vulnerabilities in routers, firewalls, servers, and other connected devices that could allow unauthorized access.
When to choose this method:
If you manage a large corporate network or store sensitive data across multiple systems, network testing should be your first line of defense to validate segmentation controls, patch management effectiveness, and exposure of “crown jewels” and other critical assets.
In a recent engagement, the CGA team discovered a web application running on a legacy server that was not yet decommissioned. The service contained a vulnerable component that allowed our operator to gain a foothold and pivot deeper into the internal network.
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People are often the weakest link in cybersecurity. Social engineering tests assess how well your staff can recognize and respond to phishing attempts, pretexting, or other manipulation tactics.
These tests often include simulated phishing campaigns, voice-phishing (“vishing”), or on-site impersonation scenarios designed to measure awareness and response processes.
When to choose this method:
If your organization frequently handles confidential data or deals with customer payments, testing your human layer is essential for validating the effectiveness of security-awareness training and incident response procedures.
In a recent phishing engagement, the CGA team generated sophisticated phishing emails that captured user credentials and MFA tokens, which led to full compromise of accounts that were presumed safe behind MFA.
Web application testing examines web apps, APIs, and portals to uncover vulnerabilities that automated scanners typically overlook. It identifies common issues such as injection flaws, authentication and configuration weaknesses, as well as deeper problems in business logic, access control, and session handling.
Testers follow structured frameworks like the OWASP Testing Guide to validate findings manually, confirm exploitability, and assess the potential business impact of each issue within the application’s unique context.
When to choose this method:
If your organization relies heavily on web platforms or customer-facing portals, this testing is critical for maintaining trust and compliance.
AI and Large Language Model (“LLM”) testing focuses on assessing the security and resilience of systems that integrate or expose machine learning components. These tests evaluate how models handle user-supplied input, enforce access controls, and protect the data used for training and inference.
Testers follow methodologies adapted from traditional application security frameworks, such as the OWASP Top 10 for LLMs and the MITRE ATLAS, to address model-specific threats. These tests combine prompt engineering techniques, adversarial inputs, and integration analysis to identify points where model behavior can be influenced or where sensitive data may be exposed.
This type of testing is as much an art as a science and requires a skilled team that understands prompt dynamics, adversarial techniques, and the application context to identify subtle model weaknesses reliably.
When to choose this method:
If your organization leverages AI-powered chatbots, assistants, or automated systems, this testing is essential for understanding how LLM components can be exploited to bypass intended functionality or leak sensitive information.
In a recent engagement, the CGA team used a multi-prompt technique (“crescendo”) to gradually bypass system guardrails, ultimately causing the model to return personally identifiable information that was embedded in its context data.
Operational Technology (“OT”) and Edge Computing testing focuses on assessing the security of distributed, device-level environments, including industrial control systems (“ICS”), Internet of Things (“IoT”) devices, smart sensors, and local data-processing nodes.
These systems often run outside traditional IT governance yet may handle critical processes and sensitive data.
Testers evaluate device and network segmentation, firmware and protocol security, authentication, and how data flows between edge nodes, OT networks, and central management systems. The goal is to identify weaknesses that attackers could leverage to disrupt operations, manipulate sensor data, or pivot between OT/edge devices into traditional IT systems.
When to choose this method:
If your business manages industrial processes, manufacturing systems, or distributed IoT infrastructure, OT and Edge testing helps ensure both uptime and data integrity.
Physical penetration testing involves real-world attempts to breach on-site security, like accessing restricted areas, tampering with servers, or removing sensitive devices, to evaluate the effectiveness of physical controls.
Testers may attempt badge cloning, tailgating, or device theft to determine whether existing safeguards and monitoring mechanisms are sufficient to detect and prevent unauthorized physical access to a corporate office or other facility.
When to choose this method:
Suppose your business handles critical infrastructure, manufacturing systems, or facilities with sensitive assets or data. In that case,
In a recent physical engagement, the CGA team tailgated into a client’s corporate office and gained access to an area where an exposed network port behind a mounted TV provided a direct path into the corporate LAN. From that foothold, the team was able to retrieve valid credentials and ultimately full domain compromise.
Cloud penetration testing evaluates the configurations, permissions, and data protections within your cloud environments, including, but not limited to, AWS, Azure, and Google Cloud. These tests identify risks like exposed storage buckets, overly permissive IAM roles, and misconfigured APIs.
Testers may review cloud control plane configurations, IAM policies, and network architectures, validate permissions between services, and attempt to exploit misconfigurations that could expose data or escalate privileges within the environment.
When to choose this method:
If your organization uses hybrid or cloud-native infrastructure, this test is vital to secure workloads and ensure compliance with frameworks like PCI DSS, ISO 27001, and SOC 2.
A Red Team simulates real-world adversaries using a combination of techniques like social engineering, technology-focused exploits, and stealth operations to evaluate how well an organization could detect, respond to, and recover from advanced threats.
These engagements often transition into “Purple” team exercises, where offensive testers (“red” team) collaborate with defenders (“blue” team) to review findings, fine-tune detection mechanisms, and improve incident response workflows.
When to choose this method:
Red and/or purple team exercises are ideal for mature organizations that have already established vulnerability management and penetration testing programs but are seeking to test the effectiveness of their entire security ecosystem, beyond just their IT systems.
At CyberGuard Advantage, our penetration testing methodology meets or exceeds leading compliance and regulatory standards, including SOC audits, HITRUST, PCI DSS, HIPAA, and ISO certifications.
Our team combines manual testing expertise with advanced tools to uncover deep-seated vulnerabilities across your IT environment, offering actionable insights and remediation guidance tailored to your business.
Curious to learn more about Penetration Testing? Explore additional Resources:
👉 Penetration Testing Guide
👉 Why penetration testing is important
👉 Penetration testing compared to vulnerability testing
The main penetration testing methods include network, web application, mobile, cloud, physical, and social engineering testing, along with specialized exercises such as red team assessments, LLM/AI testing, and OT/edge testing. Each targets different layers of your environment to provide complete visibility into your organization’s security posture.
There’s no “best method”. The right choice depends on your environment, risk appetite, and compliance needs. Many organizations combine multiple methodologies for complete coverage.
Consider factors like where your most valuable data resides, how it’s accessed, and your regulatory obligations. A cybersecurity partner like CyberGuard Advantage can help tailor a testing strategy for your business.
Yes, many organizations benefit from combining several testing types to create a layered defense strategy and validate controls across all attack surfaces.
Ready to take the next step in securing your organization? Download our comprehensive penetration testing guide to learn more about how to protect your business from the ever-present threat of cyberattacks.
Understanding penetration testing methodologies helps you make informed decisions about your organization’s cybersecurity posture. Whether you’re safeguarding your network, cloud infrastructure, or employees, selecting the right combination of tests can help prevent breaches and ensure regulatory compliance.
Partner with experts who not only identify vulnerabilities but also help you strengthen your defense before attackers do.
Learn more about our Penetration Testing Services and find out which testing approach best fits your environment.