Pen testing Methodology

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Grand Canyon University *

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Dec 6, 2023

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1 Pen Testing Methodology Adrian Andrade Grand Canyon University ITT-340 Ingrid Gaviria Due September 23, 2023
2 Phases of Compromise and Pen-testing methodology Before this begins, it is important to note that the pen-testing methodology being used here will be PTES (or Penetration Testing Execution Standard). This standard is a comprehensive framework for conducting penetration tests, and it designed to provide a structured approach for performing and reporting results. With that out of the way, there are several similarities between an attackers typical line of compromising a system, and this pen-testing methodology line of phases. An attacker will typically follow these seven steps: Reconnaissance, weaponization, delivery, exploitation, installation, command and control, and action. The goal of the first goal, called reconnaissance is to gain information about the target and find it’s vulnerabilities. This goal is completed when the attacker gains sufficient information about the system to exploit one or more vulnerabilities. The second phase (called Weaponization) is about creating malware or malicious payload that takes advantage of the vulnerability (or vulnerabilities). The goal is complete when the attacker successfully creates malware tailored to exploiting the specific weakness. The next step Is called ‘Delivery’. The goal of this step is to gain access to the target’s machine or network. This can be done by sending malware in the form of an email, or by calling the target and coaxing him/her into giving access. The goal is completed when the attacker successfully gains access to the target machine. The step after this is ‘Exploitation’. The goal of this step is to actually ex ploit the weaknesses found in the reconnaissance stage, and using the malware created in step 2. The goal is completed when the weaknesses have been exploited, and the attacker is able to gain further access into the target machine.
3 After this step is installation. The goal here is to successfully install malware and gain further control of the target machine. Malware can be installed by using trojan horses, access token manipulation, command-line interfaces, and backdoors. Each of these can be helpful in completing the goal. Goal is completed by installing further malware and gathering more control of system. After installation, the next step is command and control. The main goal here to gain more control of the system. Control to the point where the attacker can track, monitor, and guide their cyber weapons. The attacker can also try and obfuscate and commence denial of service. Obfuscate is the process in which an attacker covers their tracks and makes it seem as if nothing had occurred. Denial of service is an attack that disrupts the host machine or network in the hopes of slowing things, and distracting users. The last and final phase of the steps is Action. The goal of this step is to achieve the main reason for committing this attack in the first place. Which could be for gaining access to classified documents, attacking critical infrastructure, or for money purposes. This step can take the longest because it depends on how well the attack was performed overall. The steps for the methodology is: Pre-engagement interactions, intelligence gathering, threat modeling, vulnerability analysis, exploitation, post exploitation, and reporting.
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4 The first step of this methodology is Pre-engagement interactions. The goal of this step is get everything out of the way before the work begins. This involves scheduling the engagement, getting approval from the client, understanding client’s objectives, and defining the overall scope of the engagement. The goal is completed when all the pre-work is accomplished. The next and most crucial step is intelligence gathering. The main goal of this step is to gather intelligence about the target system. This could include data about the network infrastructure, applications, and people who use it. The goal is completed when the system is fully understood and have identified possible vulnerabilities. After intelligence gathering is the next step, Threat modeling. The goal of this step is to create a model of all potential threats that could be used to attack the system, and record them; then decide which ones are most potent and address them first. This step is done when the model is complete, and vulnerabilities catalogued. Next step is Vulnerability analysis. The goal of vulnerability analysis is to analyze the system for weaknesses. This includes identifying unpatched software vulnerabilities and misconfigurations that could be exploited. The last step of the methodology is exploitation. In this phase, the pen-tester will attempt to exploit any vulnerabilities that were identified in previous phases. As one might already deduce, the reconnaissance stage of the attacker steps, and the intelligence gathering of the pen-test methodology seem very similar. Both steps begin much earlier down the line, and have similar main goals. Which is to find vulnerabilities in the system, and to gather information. Another similarity is that they both have the same step, which is exploitation. This step is the same for both the attacker phases and the PTES methodology. Both have to do with actually exploiting the vulnerabilities found in the reconnaissance/intelligence gathering phase.
5 Should pen-testing phases be in the scope? Yes. That way if someone else (like the client for example) looks at scope, it’ll make it easier for them to know what is involved. Pen Testing Motivation Anybody who cares about their cyber security, will consider pen-testing cyber operations. This is because in order to actually better secure your organization or business’s cyber s ecurity, you have to actually know what needs securing, and whether it is sufficiently secure. And one of the best ways to do that is to pen-test. The main goal of pen-testing is find out where all the vulnerabilities are, and to simulate a mock cyber attack. This isn’t to just find vulnerabilities, it’s also to simulate the damages as well, since it is still a sort-of a legitimate attack. Being subject to leaks or something like a data breach can really motivate an organization to improve their security. And the way to do that is to pen-test. At least to some extent. Flaw Hypothesis The flaw hypothesis methodology and the pen testing methodology intersect well in the first step. Which is information gathering in flaw, and reconnaissance on pen-testing. This is because
6 they both have to do with gathering information. How could someone do a successful attack or pen-testing without knowing the system they are invading? Because OSSTMM is very focused on priority items that need to be tested, it could actually focus the pen-testing methodology steps as well. The pen-testing methodology is very generalized in that, it almost seems to say that “Yes, the goal is to test the network or host machine” but what to test specifically is never stated. OSSTM M can provide what to test, in order to better the overall pen-test. Because now, the most important and vital items will be tended to before anything else. Ethical and legal Issues If it were up to me to handle ethical and legal issues of cybersecurity, with the Christian worldview in mind, I would try to help everybody or as much people as I can. I would try to make sure my decisions were made from within the confines of the law. But honestly I don’t think I could make all legal and ethical issues align just because it can’t happen all the time. Sometimes, legal issues and ethical issues don’t align, and this can be because on one hand, a s ituation can be solved ethically, but legally, it shouldn’t be allowed. Or, a solution to an issue can be done legally, but ethically, it becomes bad or un clear. Thus, they don’t align, but I would try nonetheless because it is better when they are aligned. I think everybody would benefit from following that verse. This includes people, and organizations. I think they would benefit because we should be wise, and we should try hurt as few people as possible, because under the Christian worldview, we are all important, and valuable.
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7 References Keshri, A. (2023, April 12). Top 5 penetration testing methodologies and standards . Astra Security Blog. https://www.getastra.com/blog/security-audit/penetration-testing- methodology/#osstmm WSTG - v4.1 . WSTG - v4.1 | OWASP Foundation. (n.d.). https://owasp.org/www-project-web- security-testing-guide/v41/3-The_OWASP_Testing_Framework/1- Penetration_Testing_Methodologies Team, T. G. (2023, August 23). Cyber security: Understanding the 5 phases of intrusion . Graylog. https://graylog.org/post/cyber-security-understanding-the-5-phases-of-intrusion/ Cyber kill chains explained: Phases, Pros/Cons & Security Tactics . Splunk. (2022, November 11). https://www.splunk.com/en_us/blog/learn/cyber-kill-chains.html