BackTrack 4: Penetration testing methodologies

13 min read

A robust penetration testing methodology needs a roadmap. This will provide practical ideas and proven practices which should be handled with great care in order to assess the system security correctly. Let’s take a look at what this methodology looks like. It will help ensure you’re using BackTrack effectively and that you’re tests are thorough and reliable.

Penetration testing can be carried out independently or as a part of an IT security risk management process that may be incorporated into a regular development lifecycle (for example, Microsoft SDLC). It is vital to notice that the security of a product not only depends on the factors relating to the IT environment, but also relies on product specific security’s best practices.

This involves implementation of appropriate security requirements, performing risk analysis, threat modeling, code reviews, and operational security measurement. PenTesting is considered to be the last and most aggressive form of security assessment handled by qualified professionals with or without prior knowledge of a system under examination. It can be used to assess all the IT infrastructure components including applications, network devices, operating systems, communication medium, physical security, and human psychology.

The output of penetration testing usually contains a report which is divided into several sections addressing the weaknesses found in the current state of a system following their countermeasures and recommendations. Thus, the use of a methodological process provides extensive benefits to the pentester to understand and critically analyze the integrity of current defenses during each stage of the testing process.

Different types of penetration testing

Although there are different types of penetration testing, the two most general approaches that are widely accepted by the industry are Black-Box and White-Box. These approaches will be discussed in the following sections.

Black-box testing

The black-box approach is also known as external testing. While applying this approach, the security auditor will be assessing the network infrastructure from a remote location and will not be aware of any internal technologies deployed by the concerning organization. By employing the number of real world hacker techniques and following through organized test phases, it may reveal some known and unknown set of vulnerabilities which may otherwise exist on the network. An auditor dealing with black-box testing is also known as black-hat. It is important for an auditor to understand and classify these vulnerabilities according to their level of risk (low, medium, or high).

The risk in general can be measured according to the threat imposed by the vulnerability and the financial loss that would have occurred following a successful penetration. An ideal penetration tester would undermine any possible information that could lead him to compromise his target. Once the test process is completed, a report is generated with all the necessary information regarding the target security assessment, categorizing and translating the identified risks into business context.

White-box testing

The white-box approach is also referred to as internal testing. An auditor involved in this kind of penetration testing process should be aware of all the internal and underlying technologies used by the target environment. Hence, it opens a wide gate for an auditor to view and critically evaluate the security vulnerabilities with minimum possible efforts. An auditor engaged with white-box testing is also known as white-hat. It does bring more value to the organization as compared to the blackbox approach in the sense that it will eliminate any internal security issues lying at the target infrastructure environment, thus, making it more tightened for malicious adversary to infiltrate from the outside. The number of steps involved in white-box testing is a bit more similar to that of black-box, except the use of the target scoping, information gathering, and identification phases can be excluded. Moreover, the white-box approach can easily be integrated into a regular development lifecycle to eradicate any possible security issues at its early stage before they get disclosed and exploited by intruders. The time and cost required to find and resolve the security vulnerabilities is comparably less than the black-box approach.

The combination of both types of penetration testing provides a powerful insight for internal and external security viewpoints. This combination is known as Grey-Box testing, and the auditor engaged with gray-box testing is also known as grey-hat. The key benefit in devising and practicing a gray-box approach is a set of advantages posed by both approaches mentioned earlier. However, it does require an auditor with limited knowledge of an internal system to choose the best way to assess its overall security. On the other side, the external testing scenarios geared by the graybox approach are similar to that of the black-box approach itself, but can help in making better decisions and test choices because the auditor is informed and aware of the underlying technology.

Vulnerability assessment versus penetration testing

Since the exponential growth of an IT security industry, there are always an intensive number of diversities found in understanding and practicing the correct terminology for security assessment. This involves commercial grade companies and non-commercial organizations who always misinterpret the term while contracting for the specific type of security assessment. For this obvious reason, we decided to include a brief description on vulnerability assessment and differentiate its core features with penetration testing.

Vulnerability assessment is a process for assessing the internal and external security controls by identifying the threats that pose serious exposure to the organizations assets. This technical infrastructure evaluation not only points the risks in the existing defenses but also recommends and prioritizes the remediation strategies. The internal vulnerability assessment provides an assurance for securing the internal systems, while the external vulnerability assessment demonstrates the security of the perimeter defenses. In both testing criteria, each asset on the network is rigorously tested against multiple attack vectors to identify unattended threats and quantify the reactive measures. Depending on the type of assessment being carried out, a unique set of testing process, tools, and techniques are followed to detect and identify vulnerabilities in the information assets in an automated fashion. This can be achieved by using an integrated vulnerability management platform that manages an up-to-date vulnerabilities database and is capable of testing different types of network devices while maintaining the integrity of configuration and change management.

A key difference between vulnerability assessment and penetration testing is that penetration testing goes beyond the level of identifying vulnerabilities and hooks into the process of exploitation, privilege escalation, and maintaining access to the target system. On the other hand, vulnerability assessment provides a broad view of any existing flaws in the system without measuring the impact of these flaws to the system under consideration. Another major difference between both of these terms is that the penetration testing is considerably more intrusive than vulnerability assessment and aggressively applies all the technical methods to exploit the live production environment. However, the vulnerability assessment process carefully identifies and quantifies all the vulnerabilities in a non-invasive manner.

This perception of an industry, while dealing with both of these assessment types, may confuse and overlap the terms interchangeably, which is absolutely wrong. A qualified consultant always makes an exception to workout the best type of assessment based on the client’s business requirement rather than misleading them from one over the other. It is also a duty of the contracting party to look into the core details of the selected security assessment program before taking any final decision.

Penetration testing is an expensive service when compared to vulnerability assessment.

Security testing methodologies

There have been various open source methodologies introduced to address security assessment needs. Using these assessment methodologies, one can easily pass the time-critical and challenging task of assessing the system security depending on its size and complexity. Some of these methodologies focus on the technical aspect of security testing, while others focus on managerial criteria, and very few address both sides. The basic idea behind formalizing these methodologies with your assessment is to execute different types of tests step-by-step in order to judge the security of a system accurately. Therefore, we have introduced four such well-known security assessment methodologies to provide an extended view of assessing the network and application security by highlighting their key features and benefits. These include:

  • Open Source Security Testing Methodology Manual (OSSTMM)
  • Information Systems Security Assessment Framework (ISSAF)
  • Open Web Application Security Project (OWASP) Top Ten
  • Web Application Security Consortium Threat Classification (WASC-TC)

All of these testing frameworks and methodologies will assist the security professionals to choose the best strategy that could fit into their client’s requirements and qualify the suitable testing prototype. The first two provide general guidelines and methods adhering security testing for almost any information assets. The last two mainly deal with the assessment of an application security domain. It is, however, important to note that the security in itself is an on-going process. Any minor change in the target environment can affect the whole process of security testing and may introduce errors in the final results. Thus, before complementing any of the above testing methods, the integrity of the target environment should be assured. Additionally, adapting any single methodology does not necessarily provide a complete picture of the risk assessment process. Hence, it is left up to the security auditor to select the best strategy that can address the target testing criteria and remains consistent with its network or application environment.

There are many security testing methodologies which claim to be perfect in finding all security issues, but choosing the best one still requires a careful selection process under which one can determine the accountability, cost, and effectiveness of the assessment at optimum level. Thus, determining the right assessment strategy depends on several factors, including the technical details provided about the target environment, resource availability, PenTester’s knowledge, business objectives, and regulatory concerns. From a business standpoint, investing blind capital and serving unwanted resources to a security testing process can put the whole business economy in danger.

Open Source Security Testing Methodology Manual (OSSTMM)

The OSSTMM is a recognized international standard for security testing and analysis and is being used by many organizations in their day-to-day assessment cycle. It is purely based on scientific method which assists in quantifying the operational security and its cost requirements in concern with the business objectives. From a technical perspective, its methodology is divided into four key groups, that is, Scope, Channel, Index, and Vector. The scope defines a process of collecting information on all assets operating in the target environment. A channel determines the type of communication and interaction with these assets, which can be physical, spectrum, and communication. All of these channels depict a unique set of security components that has to be tested and verified during the assessment period. These components comprise of physical security, human psychology, data networks, wireless communication medium, and telecommunication. The index is a method which is considerably useful while classifying these target assets corresponding to their particular identifications, such as, MAC Address, and IP Address. At the end, a vector concludes the direction by which an auditor can assess and analyze each functional asset. This whole process initiates a technical roadmap towards evaluating the target environment thoroughly and is known as Audit Scope.

There are different forms of security testing which have been classified under OSSTMM methodology and their organization is presented within six standard security test types:

  • Blind: The blind testing does not require any prior knowledge about the target system. But the target is informed before the execution of an audit scope. Ethical hacking and war gaming are examples of blind type testing. This kind of testing is also widely accepted because of its ethical vision of informing a target in advance.
  • Double blind: In double blind testing, an auditor does not require any knowledge about the target system nor is the target informed before the test execution. Black-box auditing and penetration testing are examples of double blind testing. Most of the security assessments today are carried out using this strategy, thus, putting a real challenge for auditors to select the best of breed tools and techniques in order to achieve their required goal.
  • Gray box: In gray box testing, an auditor holds limited knowledge about the target system and the target is also informed before the test is executed. Vulnerability assessment is one of the basic examples of gray box testing.
  • Double gray box: The double gray box testing works in a similar way to gray box testing, except the time frame for an audit is defined and there are no channels and vectors being tested. White-box audit is an example of double gray box testing.
  • Tandem: In tandem testing, the auditor holds minimum knowledge to assess the target system and the target is also notified in advance before the test is executed. It is fairly noted that the tandem testing is conducted thoroughly. Crystal box and in-house audit are examples of tandem testing.
  • Reversal: In reversal testing, an auditor holds full knowledge about the target system and the target will never be informed of how and when the test will be conducted. Red-teaming is an example of reversal type testing.

Which OSSTMM test type follows the rules of Penetration Testing?
Double blind testing

The technical assessment framework provided by OSSTMM is flexible and capable of deriving certain test cases which are logically divided into five security components of three consecutive channels, as mentioned previously. These test cases generally examine the target by assessing its access control security, process security, data controls, physical location, perimeter protection, security awareness level, trust level, fraud control protection, and many other procedures. The overall testing procedures focus on what has to be tested, how it should be tested, what tactics should be applied before, during and after the test, and how to interpret and correlate the final results. Capturing the current state of protection of a target system by using security metrics is considerably useful and invaluable. Thus, the OSSTMM methodology has introduced this terminology in the form of RAV (Risk Assessment Values). The basic function of RAV is to analyze the test results and compute the actual security value based on three factors, which are operational security, loss controls, and limitations. This final security value is known as RAV Score. By using RAV score an auditor can easily extract and define the milestones based on the current security posture to accomplish better protection. From a business perspective, RAV can optimize the amount of investment required on security and may help in the justification of better available solutions.

Key features and benefits

  • Practicing the OSSTMM methodology substantially reduces the occurrence of false negatives and false positives and provides accurate measurement for the security.
  • Its framework is adaptable to many types of security tests, such as penetration testing, white-box audit, vulnerability assessment, and so forth.
  • It ensures the assessment should be carried out thoroughly and that of the results can be aggregated into consistent, quantifiable, and reliable manner.
  • The methodology itself follows a process of four individually connected phases, namely definition phase, information phase, regulatory phase, and controls test phase. Each of which obtain, assess, and verify the information regarding the target environment.
  • Evaluating security metrics can be achieved using the RAV method. The RAV calculates the actual security value based on operational security, loss controls, and limitations. The given output known as the RAV score represents the current state of target security.
  • Formalizing the assessment report using the Security Test Audit Report (STAR) template can be advantageous to management, as well as the technical team to review the testing objectives, risk assessment values, and the output from each test phase.
  • The methodology is regularly updated with new trends of security testing, regulations, and ethical concerns.
  • The OSSTMM process can easily be coordinated with industry regulations, business policy, and government legislations. Additionally, a certified audit can also be eligible for accreditation from ISECOM (Institute for Security and Open Methodologies) directly.


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