Penetration Testing Cheat Sheet

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Penetration testing, also known as pen testing, is a critical practice in IT security. It involves simulating cyber-attacks on your own network to identify vulnerabilities before malicious attackers can exploit them. This process helps protect sensitive data and maintain system integrity. With cybersecurity threats becoming more sophisticated and frequent, having a structured approach to penetration testing is vital for keeping your organization’s assets safe. 

This cheat sheet is intended to guide IT System Administrators and IT Security professionals  through the essential steps of a penetration test—from obtaining the necessary permissions and defining the scope of your test, to gathering information, assessing vulnerabilities, and finally, reporting your findings. Each step is designed to ensure that you can perform these tests with precision and adhere to best practices in cybersecurity. By the end of this guide, you will have a clear understanding of how to approach each phase of a penetration test and the tools that can aid in this important task. 

 Let us take a look at the steps involved in conducting penetration tests. 

Step 1: Get Permission to Test

Before beginning any penetration testing, it is necessary to secure written permission from the relevant stakeholders, such as management, IT, and security teams. This is not merely a formality; it is a critical legal requirement that protects both the tester and the organization from potential legal repercussions.  

Penetration testing involves probing for vulnerabilities which can potentially disrupt normal business operations and access sensitive data. Conducting such activities without proper authorization can be considered illegal and lead to serious consequences including lawsuits and reputational damage. 

Start by preparing a formal request that outlines the nature of the penetration test. This document should clearly specify what systems will be tested, the methods and tools you plan to use, and the reasons behind the test. It is also advisable to define the potential impacts and benefits of the test. Present this document to the upper management or the board responsible for cybersecurity within your organization. 

In addition to internal permissions, if your testing involves third-party systems or services, be sure to obtain consent from these parties as well. This might involve negotiations and the signing of agreements that outline the scope of the test and the boundaries that must not be crossed. 

Having these permissions in writing not only clarifies the scope of your tests but also secures your right to perform them, ensuring that all activities are within legal and ethical boundaries. This documentation will serve as a safeguard, providing legal defense should any questions arise regarding the legitimacy of your activities. 

Step 2: Define the Test

Defining the scope and parameters of your penetration test is essential for effective testing. Begin by specifying the systems, networks, and applications to be tested, clarifying whether the focus is on external, internet-facing systems, internal networks, or both. 

Scope and Timeline

Outline the scope clearly and establish a realistic timeline. Determine the duration of each testing phase from start to completion, ensuring that it aligns with normal business operations and minimizes disruption. 

Resources and Objectives

Identify the necessary resources, including personnel and tools, and define the test’s objectives. Specify what success looks like, such as identifying particular vulnerabilities or testing system resilience against specific attacks. 

This structured approach ensures that the test is focused, manageable, and aligned with your organization’s security goals. 

Step 3: Information Gathering

Collecting detailed information about the target environment is an essential step in the penetration testing process. This phase is important because the quality and depth of information gathered can significantly influence the outcome of the test. Accurate data collection helps in creating a targeted approach for identifying vulnerabilities. 

Leaked or Breached Account Details

Begin by examining any available data on leaked or breached accounts associated with the target. This information can provide insights into user behavior, password strength, and potential entry points for further exploitation. 

Network Topology Analysis

Utilize tools like DNSDumpster to map out the target’s network topology. This tool allows you to discover DNS records, which help in understanding the layout of the network, identifying key servers, and pinpointing entry points that are critical for the testing phase. 

Website and Social Media Analysis

Examine the target’s official websites and social media profiles. This involves looking for: 

  • Technology stack details that reveal the software and hardware components used by the target. 
  • Updates or posts that might indicate recent changes to the system architecture or expose useful operational data. 
  • Employee information that could be used to craft phishing attacks or other social engineering exploits. 

Consolidating Information

Collect all findings into a comprehensive profile of the target. This profile should include not just technical data but also contextual information that could inform your testing strategy. For instance, knowledge of a recent software deployment could suggest a focus on newly integrated systems that might not yet be fully secured. 

This thorough approach to information gathering sets the stage for effective penetration testing by providing a clear and detailed understanding of the target environment, guiding the subsequent phases of footprinting and vulnerability assessment. 

Step 4: Footprinting the Target

Footprinting is a critical phase in penetration testing where you gather and analyze information to create a comprehensive profile of the target’s digital presence. This step involves identifying the live systems, accessible hosts, and services, which lays the groundwork for effective vulnerability assessment. 

Utilizing Network Scanning Tools

Begin by deploying network scanning tools such as NMAP to scan for active devices, open ports, and services. NMAP allows you to see what systems are up and running, what services they are offering, and what types of packet filters/firewalls are in use. This information is vital for planning subsequent attack vectors and understanding the security posture of the target. 

Web and Network Services

Use tools like Spiders, web crawlers, and other footprinting software to gather additional details about the target’s web applications. Look for specific data points such as: 

  • Application entry points 
  • Scripting platforms used 
  • Server software 

Analyzing the Data

As you collect data, analyze the network’s architecture, and identify patterns or weaknesses. Pay particular attention to: 

  • Outdated systems or software that may contain known vulnerabilities. 
  • Misconfigured services that might provide an unintended entry point. 

Building the Digital Profile

The culmination of this phase is a robust digital profile that includes detailed mappings of the network’s topology and its active components. This profile should also reflect any security measures observed, such as firewall locations and intrusion detection systems. 

Footprinting not only enhances your understanding of how the target’s network is structured but also aids in tailoring the penetration testing approach to be as effective as possible. With this detailed insight, you can prioritize areas with apparent vulnerabilities for deeper testing in the vulnerability assessment phase. 

Step 5: Vulnerability Assessment

The vulnerability assessment phase is where you apply tools and techniques to identify security weaknesses within the target’s systems, as identified during the footprinting stage. This step is essential for determining which vulnerabilities are present and assessing their potential impact. 

Using Automated Scanning Tools

Employ automated scanning tools such as Legion and Greenbone Vulnerability Manager (formerly OpenVAS) to systematically identify vulnerabilities. These tools scan for a wide range of weaknesses, from outdated software and misconfigurations to potential security breaches that could be exploited by attackers. 


Legion, a user-friendly tool, automates network discovery and vulnerability scanning. It is particularly effective for identifying services running on open ports and detecting standard configuration errors that could lead to unauthorized access. 

Greenbone Vulnerability Manager

Greenbone Vulnerability Manager offers a comprehensive analysis of your network’s security posture using its extensive vulnerability tests. It continuously updates its database with the latest vulnerability tests, ensuring that it can detect new threats as soon as they become known. 

Analyzing Scan Results

Once the scans are complete, it is important to analyze the results carefully. Look for: 

  • High-risk vulnerabilities that require immediate attention. 
  • Medium and low-risk issues that could escalate under certain conditions. 
  • Any false positives that might have been flagged during the scan. 

Prioritizing Remediation Efforts

Based on the assessment, prioritize the remediation efforts, addressing vulnerabilities that have been identified. Focus on patching high-risk vulnerabilities first, as these pose the most immediate threat to your network. Plan a remediation roadmap that aligns with your organization’s capacity to mitigate these risks. 

This phase of the penetration test is vital as it provides the necessary information to understand where your security posture stands and what actions are needed to strengthen it against potential attacks. 

Step 6: Vulnerability Verification

After identifying potential vulnerabilities in the previous phase, it is essential to verify these findings to ensure they are genuine threats and not false positives. This step is important for prioritizing remediation and focusing security efforts where they are most needed. 

Verification Process

Begin by selecting the vulnerabilities identified as high-risk during the assessment phase. Use tools like the MetaSploit Framework to attempt to exploit these vulnerabilities in a controlled environment. This hands-on testing confirms whether the vulnerabilities can indeed be exploited as predicted by the assessment tools. 

MetaSploit Framework

MetaSploit is an advanced framework that allows penetration testers to develop and execute exploit code against a remote target machine. It includes a comprehensive database of publicly known exploits, making it an invaluable tool for verifying vulnerabilities. Use MetaSploit to simulate attacks and observe the outcomes, providing clear evidence of vulnerability. 

Manual Verification

In addition to automated tools, conduct manual checks where necessary. This involves deeper inspection of configurations, code reviews, and re-testing to ensure the accuracy of vulnerability findings. Manual verification is especially important for complex environments where automated tools might not adequately reflect the security landscape. 

Documentation of Findings

Document each verified vulnerability, noting how you tested it, the test results, and the potential impact on the system. This documentation is vital for the next phases of remediation and reporting. It ensures that all stakeholders understand the risks and stay informed about the security posture of their systems.


By the end of this phase, you should have a validated list of vulnerabilities. This list will guide the remediation efforts, ensuring that the team allocates resources effectively to address the most critical threats first.

Conducting the Test

After verifying the vulnerabilities, the next step is to conduct the actual penetration test using the information and insights gained from the previous phases. This stage involves simulating realistic cyber-attacks to exploit the confirmed vulnerabilities and assess the effectiveness of existing defenses. 


Using tools like the MetaSploit Framework, OWASP ZAP, and BurpSuite, attempt to exploit the verified vulnerabilities. Each tool offers unique capabilities that cater to different aspects of penetration testing: 

  • MetaSploit Framework is effective for deploying and testing exploits in a controlled environment. 
  • OWASP ZAP provides capabilities for testing web applications for vulnerabilities like SQL injection and cross-site scripting. 
  • BurpSuite is excellent for testing the security of web-based applications and performing manual security testing. 


Apply various techniques based on the vulnerabilities identified: 

  • SQL Injection: Exploit flaws in SQL databases to execute unauthorized database commands. 
  • Buffer Overflow: Test the limits of data storage in applications to trigger errors and potential exploits. 
  • Brute Force Attacks: Attempt to guess passwords using systematic checks from possible combinations to breach systems. 

Observation and Adaptation

During the test, closely monitor how the system responds to each attack. This observation will help you understand the resilience of the system and identify any additional vulnerabilities or weaknesses in the network’s defenses. 


Document every step of the test, including the tools used, the techniques applied, the success of each exploit, and how the system responded. This comprehensive documentation is important for the final reporting and will provide valuable insights into improving the security posture. 

Review and Repeat

Review the test outcomes and determine if further testing is needed. Initial tests sometimes reveal additional vulnerabilities or indicate that more sophisticated or different approaches are required.

This phase is critical for understanding the real-world effectiveness of the target’s security measures and provides a direct assessment of how well the current defenses can withstand an attack. 

Step 7: Reporting

The final phase of the penetration testing process is to compile and present a comprehensive report detailing the findings from the test. This report is important for stakeholders to understand the security vulnerabilities, the potential impacts of these weaknesses, and the necessary steps to mitigate them. 

Structure of the Report

A well-organized report should include the following sections: 

  • Executive Summary: Provide a high-level overview of the testing process, key findings, and recommendations. This section helps executives understand the implications without the technical details.
  • Methodology: Describe the methods and tools used during the penetration testing. This section reassures stakeholders of the thoroughness of the testing process. 
  • Detailed Findings: Present each vulnerability discovered during the testing phases. Include detailed descriptions, the potential impact of the vulnerability, and proof of concept (if applicable). Organize this section in order of the severity of the findings. 
  • Recommendations: For each vulnerability, suggest remedial actions or mitigation strategies. These recommendations should be practical, clearly explained, and prioritized based on the risk they pose. 
  • Appendices: Include any supporting materials such as logs, code snippets, screenshots, and tool outputs that can validate the findings and provide technical stakeholders with the depth of information needed for remediation. 


Compile the report and then present the findings to the relevant stakeholders. This presentation should be both informative and persuasive, stressing the importance of taking prompt action to mitigate the identified risks. Ensure that the communication style and depth of information are appropriate for the audience, whether technical or non-technical. 


Finally, schedule follow-up meetings to discuss the implementation of the recommended security measures. Maintaining engagement with the stakeholders is essential to ensure that they address the vulnerabilities and discuss any further testing that might be necessary after remediation efforts.

This reporting phase is not just a formality but a vital component of the penetration testing process. It ensures that people act on the findings, enhances the organization’s security posture, and provides a basis for future tests.


In conclusion, the “Penetration Testing Cheat Sheet” serves as a comprehensive guide for professionals looking to secure their systems through ethical hacking. This resource offers a structured approach to penetration testing, beginning with the essential step of obtaining permission, defining the test scope, and meticulously gathering information about the target. By following the steps outlined—from initial data collection to detailed vulnerability assessment and exploitation—the cheat sheet ensures that testers can effectively identify and mitigate potential security risks. Moreover, the emphasis on legal compliance and thorough reporting underscores the necessity of maintaining ethical standards in cybersecurity efforts. Ultimately, this cheat sheet not only aids in fortifying systems but also enhances the overall security posture, making it an invaluable tool for IT security teams and consultants aiming to protect their digital assets against evolving threats. 

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