Understanding Common Penetration Tests: A Business Guide

Penetration testing, or “pentesting,” is a critical component of a robust cybersecurity strategy. It involves simulating cyberattacks on your systems to identify and address vulnerabilities before malicious actors can exploit them. But not all pen tests are created equal. Depending on the scope, objectives, and environment, different types of penetration tests are needed to thoroughly assess your organization’s security posture. In this article, we will explore five common types of penetration testing: External, Internal, Web Application, Social Engineering, and Physical. We will also touch on special considerations for industries regulated by HIPAA and PCI-DSS.

External Penetration Testing

External pentests are a network security test which focuses on your organization’s internet-facing systems, such as web servers, firewalls, and other entry points. The goal is to identify vulnerabilities that could be exploited from outside the network, usually by a remote attacker.

The tester conducts this assessment from outside your network, often simulating the tactics, techniques, and procedures (TTPs) of external cybercriminals. This may involve scanning for open ports, probing for weaknesses in web applications, and testing the strength of your firewalls and other perimeter defenses.

External pentesting is essential for any organization with internet-facing infrastructure. It helps identify your public attack surface and ensures that your external defenses are robust enough to withstand cyberattacks that originate from the outside world.

A common question we receive from clients is, “What if Tac 9 gains internal access during the course of our external penetration test?”

The general approach is that our tester will immediately communicate this finding to you. Gaining internal access during an external penetration test is a significant event, as it indicates a potential weakness in your external defenses that could be exploited to breach the internal network.

Once we inform you of this development, we can proceed in one of two ways, depending on your objectives and priorities:

1. Continue Exploring the Depth of the Finding: If your goal is to understand the full extent of the breach and the potential damage an attacker could cause after gaining internal access, our tester can shift focus to an internal penetration test. This would involve simulating further actions that an attacker might take within your internal network, such as privilege escalation, lateral movement, and data exfiltration.
2. Return to the External Attack Surface: Alternatively, if your primary objective is to complete the assessment of your external attack surface, we will document the internal access finding and return to evaluating the remaining external vulnerabilities. This approach ensures a comprehensive evaluation of your external defenses while flagging the internal access issue for further investigation at a later stage.

In either scenario, we ensure that you are fully informed and involved in the decision-making process. Our priority is to align our testing with your security goals and provide you with the insights needed to strengthen your overall cybersecurity posture.

Internal Penetration Testing

Internal pen tests focus on identifying vulnerabilities that could be exploited by insiders or attackers who have gained a foothold in your internal network. This might include employees, contractors, or attackers who have breached the external perimeter.

The tester typically simulates an attack from within the network. They might start with limited access, such as that of a regular employee, and attempt to escalate privileges, access sensitive data, or move laterally across the network. The focus is on understanding what an attacker could do with access to your internal resources.

Internal pen testing is crucial for organizations which operate under the “assume breached” detection-engineering model or have concerns about insider threats, rogue employees, contractors, or attackers who have bypassed external defenses. It is also vital for assessing the effectiveness of internal security measures like network segmentation, user access controls, and monitoring.

Web Application Penetration Testing

Web application pen tests focus specifically on applications accessed via a web browser. This includes anything from simple websites to complex web-based platforms that manage critical business operations.

The pen tester will simulate attacks that target the application’s features, user inputs, and APIs (complex API’s may require an assessment separate from a web application test). This might involve testing for SQL injection, cross-site scripting (XSS), authentication flaws, and other common web application vulnerabilities. The goal is to determine how an attacker could gain unauthorized access, manipulate data, or disrupt service.

Any organization that relies on web applications, especially those that handle sensitive data or business-critical processes, should regularly conduct web application penetration testing. This is crucial for maintaining the security and integrity of these applications.

Social Engineering Penetration Testing

Social Engineering Penetration Testing simulates attacks that exploit human psychology rather than technical vulnerabilities. It involves tricking employees or other insiders into revealing sensitive information, granting access, or performing actions that compromise security similar to the recent attacks in Las Vegas (Las Vegas Review-Journal).

The primary objective is to evaluate the organization’s susceptibility to social engineering attacks, such as phishing, pretexting, baiting, or tailgating. The test helps determine the effectiveness of employee training and the robustness of security policies related to human interactions.

Common methods include sending phishing emails to employees, calling employees while impersonating IT support, or attempting to gain physical access to restricted areas by pretending to be a trusted individual. The tester records how employees respond to these simulated attacks and whether any sensitive information is disclosed or unauthorized access is granted.

The test report typically includes an analysis of employee responses to the attacks, identification of any weaknesses in security awareness, and recommendations for improving training and policies to reduce the risk of successful social engineering attacks in the future.

Physical Penetration Testing

Physical Penetration Testing assesses the security of an organization’s physical infrastructure, including buildings, data centers, and other secure areas. The goal is to identify vulnerabilities that could allow unauthorized personnel to gain physical access to sensitive locations or assets.

The main objective is to test the effectiveness of physical security measures, such as locks, access control systems, surveillance cameras, and security personnel. The test evaluates whether an attacker could bypass these measures to steal assets, install malicious hardware, or access confidential information.

The test typically involves attempts to enter restricted areas without proper authorization. Methods may include lock-picking, bypassing security checkpoints, tailgating behind authorized personnel, or posing as maintenance staff. The tester may also attempt to plant rogue devices, such as keyloggers or network taps, in secure areas.

The test report includes details of the methods used to bypass security, the specific vulnerabilities identified, and recommendations for strengthening physical security. This may involve upgrading locks, improving access control systems, enhancing security awareness among staff, or restructuring security protocols.

Other Types of Penetration Tests

Several specialized types of pentests have emerged to address the growing complexity of modern IT environments. IoT Penetration Testing targets the security of Internet of Things devices and ecosystems, identifying vulnerabilities that could allow attackers to exploit connected devices such as smart home systems, industrial sensors, or healthcare devices. Similarly, Mobile Application Penetration Testing focuses on the security of mobile apps on platforms like iOS and Android, ensuring that apps do not expose sensitive data or allow unauthorized access through insecure code or configurations.

Cloud Penetration Testing is critical as organizations increasingly rely on cloud services for data storage and processing. This type of testing examines the security of cloud environments, including the configurations of cloud instances, access controls, and the interaction between cloud services and on-premise systems. Wireless Penetration Testing, on the other hand, assesses the security of an organization’s wireless networks, identifying risks such as weak encryption, rogue access points, or insecure wireless protocols that could be exploited by attackers within range of the network. These specialized pentests are essential for securing the diverse range of technologies that modern organizations depend on.

Compliance Considerations: HIPAA and PCI-DSS

Certain industries, particularly those dealing with sensitive personal and financial data, are subject to stringent regulations that mandate regular penetration testing. Two of the most prominent regulations are HIPAA and PCI-DSS, each with specific requirements that must be met to ensure compliance.

HIPAA Penetration Testing Requirements

While HIPAA does not explicitly mandate penetration testing, it requires covered entities to conduct regular risk assessments. Penetration testing is widely recognized as a best practice for fulfilling this requirement, as it provides a thorough evaluation of the organization’s security posture and helps identify potential vulnerabilities that could lead to a breach of PHI such as those seen in the recent Change Healthcare (a United Healthcare subsidiary) ransomware attack (click here for more information).

When conducting penetration tests in a HIPAA-regulated environment, it is critical to focus on areas where PHI is stored, transmitted, or processed. Special attention should be given to ensuring that systems are appropriately hardened, access controls are stringent, and encryption is properly implemented.

PCI-DSS Penetration Testing Requirements

PCI-DSS has explicit requirements for penetration testing, outlined in Requirement 11.3. Organizations must conduct both internal and external penetration tests at least annually and after any significant changes to the network. The tests must cover all network segments and systems that are part of, or connected to, the cardholder data environment (CDE).

PCI-DSS penetration testing must be thorough and include not only traditional infrastructure but also web applications and APIs that handle payment information. The scope should be carefully defined to ensure that all components of the CDE are tested. Additionally, the testing must be performed by qualified individuals, either internal staff with appropriate credentials or external specialists.

Before contracting a service provider to perform a PCI-DSS penetration test, ensure the provider is a certified “Qualified Security Assessor” (QSA) to ensure the penetration test will be accepted for compliance.

Tac 9 Security is NOT a certified QSA. We will conduct supporting Penetration Testing to ensure the safety, security and functionality of your application or system, but we cannot provide a penetration test that meets PCI requirements. Many companies will offer these assessments without certification and it’s important that you ensure the testing meets your objectives.

To verify if your provider is a certified QSA, use this link here to the PCI Security Standards website.

Conclusion

Understanding the different types of penetration testing is essential for any organization looking to strengthen its cybersecurity defenses. Whether you need to secure your internal network, protect your web applications, or comply with stringent industry regulations like HIPAA and PCI-DSS, choosing the right type of penetration testing is crucial. Regular testing not only helps in identifying and mitigating vulnerabilities but also in maintaining compliance and protecting your organization’s reputation. At Tac 9 Security, we specialize in a comprehensive range of penetration testing services tailored to meet the unique needs of your business. Contact us today at 855.618-9765 to learn how we can help you enhance your security posture and achieve compliance with industry regulations.