Final Penetration Test Proposal Deliverable 4

Penetration Test Proposaldeliverable 4 Final Penetration Test Proposa

This document presents the final penetration test proposal for Haverbrook Investment Group, detailing the comprehensive methodology intended to assess the security posture of the organization’s information systems. The proposal encompasses the scope of the test, rules of engagement, reconnaissance strategies, scanning procedures, techniques for gaining access, maintaining access, and covering tracks, all conducted within an ethical framework that ensures responsible testing practices.

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Introduction

In today’s digital age, organizations like Haverbrook Investment Group face increasing cybersecurity threats that jeopardize sensitive financial information, client data, and operational integrity. Conducting a penetration test (pen test) is a vital security measure to evaluate the effectiveness of existing defenses, identify vulnerabilities, and enhance the organization’s resilience against cyberattacks. This proposal outlines a structured approach to performing a controlled and ethical penetration test, aimed at discovering and mitigating security gaps within the organization’s systems.

Scope and Rules of Engagement

The scope of this penetration test includes all publicly accessible and internal systems associated with Haverbrook Investment Group, such as web applications, network infrastructure, servers, and endpoints. The testing will be confined within predefined boundaries to prevent disruptions to business operations. The rules of engagement specify that testing activities will be conducted during scheduled windows, with explicit authorization from the organization’s management, and that data confidentiality, integrity, and availability will be maintained throughout the process. The testers will avoid destructive testing methods unless explicitly authorized, ensuring minimal impact on daily operations.

Checklist and Ethical Considerations

The testing requirements include comprehensive vulnerability scanning, information gathering, exploitation attempts, post-exploitation activities, and meticulous documentation. Ethical principles such as respect for confidentiality, non-disruption of services, and adherence to legal standards will guide all testing phases. The testers are committed to reporting findings promptly, providing recommendations, and ensuring that all activities are performed with integrity and transparency.

Reconnaissance Plan

The reconnaissance phase lays the groundwork for the penetration test by collecting as much information as possible about the target organization. This involves both passive and active methods. Passive reconnaissance includes analyzing publicly available information such as DNS records, website metadata, social media, and public databases, which help identify potential attack vectors without alerting the organization. Active reconnaissance involves direct probing of the target’s network, such as port scanning and system fingerprinting, to uncover live hosts, open ports, services, and system configurations. This structured approach ensures a comprehensive understanding of the target’s landscape before exploiting vulnerabilities.

Reconnaissance Methods

Passive reconnaissance methods include analyzing WHOIS records, infrastructure footprint mapping, and monitoring public sources for data leaks. These techniques minimize the risk of detection. Active methods involve tools like Nmap for port scanning, Netcat for banner grabbing, and enumeration scripts to identify running services, user accounts, and configurations. The methodology follows a logical sequence to gather and verify information efficiently, ensuring that each step informs the next. For example, identifying open ports guides targeted service enumeration, while discovering server information helps pinpoint potential vulnerabilities.

Scanning Plan

The scanning phase aims to identify vulnerabilities within discovered services and systems. Techniques such as vulnerability scanning with tools like Nessus or OpenVAS will be employed to detect known security weaknesses. The process includes identifying outdated software versions, misconfigurations, and unpatched vulnerabilities. The results will be analyzed to prioritize remediation efforts. Additionally, targeted scans for specific known vulnerabilities (e.g., CVEs) related to the identified services are crucial to uncover exploitable weaknesses that could jeopardize the organization’s security posture.

Tactics, Techniques, and Procedures

Information gathering focuses on usernames, system names, shares, and running services, which can be leveraged for further exploitation. Software like Metasploit, Burp Suite, and custom scripts will be used to automate enumeration tasks. For example, Metasploit modules will test for known vulnerabilities, while scanning scripts will harvest information about network shares and configurations. The process includes gathering credentials, exploiting weak passwords, and extracting configuration data, all conducted in accordance with ethical guidelines to avoid any disruption.

Gaining Access

The next phase involves exploiting identified vulnerabilities to gain initial access. Resources such as outdated web applications, unpatched operating systems, or misconfigured services are prime targets. Vulnerabilities verified through references like the National Vulnerability Database (NVD) will be exploited using tools like Metasploit, SQL injection techniques, or credential stuffing. The objective is to demonstrate that these vulnerabilities can be exploited in real-world scenarios, providing concrete evidence for remediation.

Techniques and Software

Techniques include exploiting known software vulnerabilities, misconfigurations, and weak authentication mechanisms. Software tools like Metasploit Framework will facilitate automated exploitation, while custom scripts may be employed for specific attack vectors. For example, SQL injection exploits could be used against vulnerable web applications, and brute-force tools may test password strength. All techniques are chosen for their effectiveness and to simulate realistic attacker behaviors.

Maintaining Access

Once access is gained, maintaining a presence within the system ensures ongoing testing capacity and demonstrates potential persistent threats. Techniques include creating backdoors, utilizing tools such as Netcat or Meterpreter, and establishing administrative accounts. These methods are executed carefully to avoid detection and to assess the persistence mechanisms an attacker could employ.

Covering Tracks

To simulate an attacker intent on remaining undetected, methods to cover tracks will be employed. These include deleting logs, clearing command history, and modifying timestamps, using scripts like auditctl or LogCleaner. Software tools designed for concealment will be used judiciously to analyze the effectiveness of existing security measures and to inform defensive strategies. The purpose is to evaluate how well the organization can detect and respond to stealthy attacks.

Conclusion

This structured penetration testing approach offers a comprehensive assessment of Haverbrook Investment Group’s cybersecurity resilience. By following ethical principles and employing proven methodologies, the testing will uncover vulnerabilities, help prioritize remediation efforts, and strengthen defense mechanisms against future cyber threats. Continuous improvement in security posture depends on such meticulous evaluation and proactive defense strategies.

References

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