Penetration Testing Types: Which One Your Project Needs

Penetration testing, often called pen testing, is a meticulously controlled assessment process to measure a system's security by detecting and exploiting its vulnerabilities. This process involves uncovering weaknesses within an organization's networks, databases, and critical information systems.

No company is impervious to risks and vulnerabilities. Despite robust digital infrastructures and stringent cybersecurity measures, residual risk always lingers. This is why many organizations incorporate penetration testing within their risk assessment and security strategies. Security experts conduct these tests—essentially stepping into the role of a hacker—to grasp the intricacies of an organization's infrastructure and unearth potential risks and vulnerabilities.

Explore the Black Box, White Box and Grey Box methodologies in this blog post and uncover how each aligns with distinct security needs. Let's get started!

Why Regular Penetration Testing Is Important?

The landscape of cyber threats continues to intensify in both frequency and severity, posing significant risks to businesses across all scales. Such formidable attacks include ransomware, phishing, and web-based assaults such as cross-site scripting (XSS) and SQL injection.

Penetration testing operates from a hacker's viewpoint, seeking to preemptively uncover and address cybersecurity vulnerabilities before malicious actors exploit them. Unlike traditional security testing approaches that merely signal potential issues requiring investigation, penetration testing reveals confirmed vulnerabilities and their potential impact on business operations.

Penetration Testing Types: What Are The Different Approaches To Penetration Testing?

When it comes to safeguarding digital fortresses, penetration testing stands as a fundamental practice. It's the go-to method for scrutinizing system security, effectively unveiling its weaknesses when executed correctly. Penetration testers adopt three distinct approaches in conducting various types of pen tests:

Black Box Testing

In a black-box testing assignment, the penetration tester assumes the role of an average hacker devoid of internal knowledge about the target system. This approach involves dynamic analysis of running programs and systems within the target network, employing automated scanning tools and manual methodologies. Their focus lies in gathering data about the system, knowing only the expected outcomes without delving into the intricacies of how these outcomes are achieved. It's a scenario where the tester doesn't inspect programming codes but emphasizes the expected end results.

The objective of a black-box penetration test is to identify vulnerabilities exploitable from outside the network.

The limited information available to the tester makes black-box penetration tests swift to execute, contingent on the tester's ability to locate and exploit vulnerabilities in outward-facing services. However, a drawback is that if the perimeter isn't breached, vulnerabilities in internal services might remain undetected and unpatched.

Grey Box Testing

Gray-box penetration testing, also known as insider attack simulation, represents a hybrid approach where the penetration tester possesses partial knowledge, including network diagrams, documentation, or limited access to the internal network but lacks complete system access. For instance, in web application pentesting, it's common to provide the testing team with specific test credentials, indicative of a gray-box approach. Unlike black-box testing, the tester has more than just an external understanding but less insight compared to white-box testing.

The primary aim of gray-box penetration testing is to offer a more targeted and streamlined evaluation of a network's security compared to black-box assessments. Leveraging design documentation, pen-testers assess high-risk systems right from the outset, bypassing the need to deduce this information independently. Accessing an internal system account allows for examining security measures within the fortified perimeter, mirroring an attacker's tactics with prolonged network access.

White Box Testing

White-box penetration testing equips security engineers with complete access to the target scope, encompassing credentials, network diagrams, documentation, and source code. In this method, the tester is equipped with an extensive array of system and/or network information, including schema, source code, OS details, and IP addresses.

White-box penetration testing offers a thorough assessment of both internal and external vulnerabilities. The primary focus of white box testing revolves around comprehending the application's functionality and attempting to breach it armed with knowledge of the source code. This contrasts with black-box testing, where access to the source code is unavailable to the tester.

Penetration Testing Methods

External penetration testing

External testing involves assessing a company's internet-visible assets, such as web applications, API, corporate websites, email systems, and domain name servers, through a process known as external penetration testing. The primary objective is to identify and address vulnerabilities that any external attacker with internet access could exploit. It simulates an attack conducted by an "ethical" hacker against an organization's external web servers, website hosting, or internet-connected devices.

In external network penetration testing, the focus is on evaluating the security of systems that interact directly with the Internet. This includes fortifications guarding technologies like websites, databases, web applications, and File Transfer Protocol (FTP) servers – typically called the organization's "perimeter security."

Penetration testers operate from an outsider's perspective, attempting to gain access to critical business systems and data without prior knowledge or access. This type of testing is invaluable as it replicates the techniques used by external attackers, aiming to determine the system's resilience against breaches.

Internal Penetration Testing

Internal penetration testing simulates the actions of an attacker who has already infiltrated the internal network. These assessments shed light on how insider threats—whether deliberate or unintentional—might jeopardize the organization.

Security teams or authorized users simulate insider attacks. A common example involves accessing a compromised staff or team member's account, often due to a phishing attack. This approach assesses the potential harm caused by an employee with elevated privileges. From an "insider" perspective, the objective is to uncover potential pathways for stealing sensitive information or disrupting organizational operations.

​​Social Engineering Testing

Social Engineering Testing is a crucial penetration testing method with the primary objective of assessing an organization's susceptibility to human manipulation and psychological exploitation. Unlike traditional testing that focuses solely on technical vulnerabilities, social engineering examines the effectiveness of an organization's human-centric security measures.

The primary goal of social engineering testing is to evaluate how well employees can resist deceptive tactics and recognize potential security threats. This includes gauging their awareness of phishing attempts, unauthorized access requests, or other social engineering attacks.

Red Team Assessment

Red teams adopt an offensive defense strategy, simulating external attacks, while blue teams concentrate solely on defense. This setup leads to a clash between the red and blue teams, each striving to identify weaknesses in the other's defenses.

Their objective is to simulate real-world attacks by attempting to breach an organization's defenses, uncover vulnerabilities, and exploit security weaknesses across digital, social, and physical domains. Red team exercises offer a critical perspective on an organization's resilience against sophisticated attacks, testing its ability to detect, respond to, and recover from real-world threats.

Physical Testing

In this assessment, cybersecurity experts focus on identifying and addressing potential "physical threats," encompassing attacks that involve physical access to locations. These simulations might include picking locks, stealing devices, or employing social engineering tactics to persuade an employee to grant access to a server room.

The objective is to uncover weaknesses in physical barriers and security measures, such as breaches in secure procedures, malfunctioning intrusion alarms, vulnerabilities in perimeter fences, or assessing the efficacy of security personnel.

Areas of Pen Testing: 8 Types of Penetration Testing

Wireless penetration testing

Wireless network penetration testing evaluates the vulnerability of your computer network to potential intrusions. It refers to scrutinizing Wi-Fi security, differentiating from assessments on Bluetooth, BLE, ZigBee, or other radio signal-based protocols (which can also undergo security assessments but require specialized tools like software-defined radio).

The primary aim of wireless penetration testing is to expose and exploit vulnerabilities within Wi-Fi networks, enabling unauthorized access to an organization's network. The process involves employing diverse tools and methodologies to scan for wireless networks, detect weaknesses, and imitate active attacks (such as capturing and cracking WPA2 handshakes) or passive attacks, including creating rogue access points to obtain wireless credentials.

Organizations can employ penetration testing to find the vulnerability of their Wi-Fi networks to potential attacks. Evaluating access points, wireless clients, and diverse wireless network protocols (like Bluetooth, LoRa, Sigfox) uncovers common vulnerabilities such as encryption flaws and weaknesses in Wi-Fi Protected Access (WPA) keys.

IoT penetration testing

The Internet of Things (IoT) represents a complex interplay among various conventional elements—from cloud services to operating systems and applications—integrated with an array of smart devices interconnected within the same network.

The primary objective of IoT penetration testing is to uncover vulnerabilities and weaknesses inherent in IoT devices and systems, proposing recommendations to enhance their security posture. This involves various facets such as identifying open ports with misconfigurations, unpatched software, discovering factory-set "backdoor" accounts, default passwords, extracting firmware to detect security issues, bypassing anti-tamper measures, and finding avenues to gain access to the device or jailbreak it through methods like JTAG/UART/SPI.

Web application testing

Web application penetration testing is a comprehensive evaluation aimed at assessing the security posture of web-based systems. This assessment follows a structured framework, often beginning with a baseline checklist such as the OWASP Top 10 for Web Applications.

The penetration tester meticulously investigates the web application, searching for vulnerabilities like SQL injection, cross-site scripting, and cross-site request forgery. Upon discovery, these vulnerabilities are rigorously examined to ascertain whether they could be exploited to gain access to critical information or control over the web application.

Web application penetration testing encompasses the detection of vulnerabilities related to data validation, integrity, authentication, user session management, and more. Testing a web application typically involves three phases: reconnaissance, vulnerability identification, and attempts to exploit these vulnerabilities to access applications or backend systems illicitly.

Mobile application penetration testing

Mobile application penetration testing involves comprehensively evaluating mobile apps and their associated APIs. Penetration testing experts employ both manual and automated tools to detect vulnerabilities, specifically in mobile apps, known for their inherent high-risk nature.

Penetration testing aims to uncover intricate security concerns, such as business logic flaws, deployment configurations, and injection vulnerabilities within apps running on diverse operating systems like Android, iOS, and Windows UI. These assessments often align with OWASP Top 10 Mobile guidelines and, for more comprehensive evaluations during Software Development Life Cycle, follow the OWASP Mobile Application Security Verification Standard (MASVS).

Social engineering penetration testing

Social engineering penetration testing involves meticulously evaluating the security awareness of a company's employees to detect vulnerabilities exploitable by potential attackers. These tests create scenarios where an attacker deceives an employee into divulging sensitive information or granting unauthorized access to critical systems.

In contrast to other penetration testing methods focused on technological weaknesses, social engineering aims to compromise organizational security by exploiting human psychology. This multifaceted approach can manifest remotely, like attempting to extract sensitive information through phishing emails or phone calls, or on-site by trying to gain physical facility access. Regardless of the approach, the objective remains consistent: manipulating individuals, often employees, into divulging valuable information.

Network service testing

Network penetration tests focus on uncovering weaknesses in your network infrastructure, whether it's on-site or within cloud environments. This test is critical in safeguarding your organization's sensitive data. It involves assessing configurations, encryption, and patching vulnerabilities to understand potential attack paths. This involves examining servers, firewalls, routers, printers, switches, and workstations.

By identifying these weaknesses, it helps prevent potential cyberattacks that take advantage of misconfigured firewalls, attacks targeting switches or routers, and various DNS, proxy, or man-in-the-middle (MiTM) attacks. Network testing involves several tasks, such as bypassing firewalls, testing routers, evading intrusion prevention/detection systems (IPS/IDS), footprinting DNS, scanning open ports, and trying SSH attacks.

API penetration testing

An API penetration test involves uncovering vulnerabilities within an application programming interface (API), emulating the actions of a potentially malicious user to assess the application's susceptibility to attacks.

The process of API penetration testing closely resembles web application penetration tests. Similar tooling is utilized, often employing tools like Burp Suite and OWASP ZAP, occasionally paired with Postman or Swagger, mirroring common web app penetration testing practices. Notably, API penetration testing has a dedicated segment in the updated 2023 edition of the OWASP Top 10, emphasizing its importance.

Specific considerations unique to API testing, such as assessing authentication and authorization mechanisms, as well as addressing critical attack vectors like mass assignment, access control issues (such as IDORs and BOLAs), rate limit testing, and more, are crucial aspects during API penetration tests.

Cloud penetration testing

Cloud penetration testing aims to uncover and exploit security weaknesses in infrastructure and applications, particularly Software as a Service applications, housed within public cloud platforms like Amazon Web Services, Microsoft Azure, and Google Cloud Platform (GCP). The objective is to gain unauthorized access to sensitive data and get control over the targeted infrastructure.

Furthermore, cloud services such as AWS Cognito, Azure AD, S3 buckets, RDS, among others, might possess misconfigurations and issues. Hence, it's vital to engage an experienced pentester who can identify these services, comprehend their nuances, and harness them effectively during the assessment.

Penetration Testing Steps

A typical penetration test involves several key phases. Now, different types of penetration tests might focus more on some phases while skipping others, depending on their specific aims and scopes. However, these phases might shift a bit depending on the provider and the type of testing you're aiming for.

1. Preparation: In this phase, both the tester and the client hash out the details: what systems will be tested, the methods the tester uses, and any additional goals and legal considerations.
2. Reconnaissance: The tester gets to work gathering information on the subject of the test. That includes everything from the people involved to the tech they use and details about their systems.
3. Vulnerability assessment: Armed with the comprehensive information gathered, the testers adopt the perspective of real attackers. Their focus shifts towards identifying and evaluating potential weaknesses within the client's system.
4. Exploiting Vulnerabilities: At this stage, any vulnerabilities identified are taken advantage of, but always within the scope set out in the prep phase.
5. Post-Exploitation Phase: Once the pentest team exploits the targeted system, they try to collect as much information as possible from it and find a way to elevate privileges or check for opportunities to establish persistent access to the system or application.
6. Report Time: The tester prepares a report for the client detailing the methods used, which vulnerabilities were exploited, recommendations for fixing them, and other important information.
7. Check-In: The tester might return to re-run the tests to ensure those weaknesses are patched up. This step isn't always part of the process but might be requested by the client for added peace of mind.

TechMagic is Your Pentesting Service Partner

Identifying vulnerabilities is just the starting point. The longevity and effectiveness of your compliance or cybersecurity program hinge on consistent maintenance and periodic reviews. This approach ensures its adaptability in countering new and evolving threats over time.

Our penetration testing services experts aid various industries in uncovering and rectifying intricate vulnerabilities across internal and external infrastructure, wireless and web applications, mobile apps, network structures, configurations, and beyond. We understand that not all architectures or applications fit into standard molds, requiring a flexible testing methodology to develop a solution that best suits your organization's needs.

FAQs

1. How do I know which penetration testing type is right for my organization in 2024?

   Choosing the appropriate penetration testing type depends on several factors like the size of your organization, the complexity of your IT infrastructure, compliance requirements, and the nature of your business operations. Engaging with a cybersecurity expert to assess your specific needs and risks can help determine the most suitable type of penetration testing for your organization.

2. When should you conduct a penetration test?

   The most crucial period for a pen test is before a breach occurs. In case of a breach, a post-breach remediation pen test becomes essential to validate the effectiveness of implemented mitigations. Best practices advocate for conducting pen tests during the development phase or before the system goes into production.

3. How often should you perform a pen test?

   Organizations should schedule security testing at least annually, with additional assessments after major infrastructure changes, before product launches, or during mergers/acquisitions. Larger entities with substantial personal or financial data or stringent compliance mandates should consider more frequent penetration tests.