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Penetration Test Proposal Details

For this assignment, you will play the role of a penetration tester for a fictional company, Centralia Security Lab. Your task is to develop a penetration testing proposal for your new client, Haverbrook Investment Group,

Welcome to Centralia Security Lab!

Centralia Security Lab has been hired by Haverbrook Investment Group to perform penetration testing on its systems. As a pen tester, you have been assigned to write the plan for what Centralia will do in the testing.

Your proposal should include the “rules of engagement” (agreement outlining the framework for the penetration testing) and outline how you would go through the five phases of hacking

Network Layout

Penetration testing involves a series of activities undertaken to identify and exploit security vulnerabilities. It helps to confirm the effectiveness or ineffectiveness of the security measures that have been implemented. According to EC-Council, the three phases of penetration testing include the preattack phase, attack phase, and postattack phase.

The Penetration Test Proposal consists of four related assignments that are submitted throughout the course. The submissions align with the five phases of ethical hacking.

The Penetration Test Proposal will be submitted in four one- to four-page deliverables. Then, you will submit a final deliverable with all the sections combined at the end of the course:

• Rules of Engagement
• Reconnaissance Plan and Scanning Plan
• Gaining Access Plan
• Maintaining Access Plan, Covering Your Tracks Plan, and Final Report.

Deliverable 1: Rules of Engagement

The first deliverable of the Penetration Test Proposal is the rules of engagement (ROE) document, a formal document that outlines the objectives, scope, methodology, and overall test plan agreed upon by the penetration testers and client system administrators.

Penetration testing can cause complications such as network traffic congestion, system downtime, and may cause the same vulnerabilities and compromises it was designed to prevent. Due to the potential consequences of penetration testing, it is vital to agree on a comprehensive ROE before testing.

For your one- to two-page ROE deliverable, consider the following:

• How will you identify Haverbrook Investment Group’s network characteristics, expectations, constraints, critical systems, and other relevant information?
• What are your preliminary engagement activities with regard to scheduling, scope, and key stakeholders?
• What will you use to establish a binding agreement between Centralia Security Lab and Haverbrook Investment Group?
• How will you determine the services, targets, expectations, and other logistics that will be covered during the Rules of Engagement section?
• How will you explain to Haverbrook that the tools and techniques to be used in the penetration test will not corrupt data, violate privacy, and are in compliance with industry standards and any applicable laws and regulations?

Use the Rules of Engagement Template below to record your work

Penetration Test Proposal

Deliverable 1: Rules of Engagement

Name:

Course Number and Section:

Instructor:

Date:

Rules of Engagement

Overview

Include a brief description of the penetration test project.

Scope

Discuss the scope of the penetration test (pen test).

Checklist

Provide a list of the testing requirements.

Ethical Considerations

Describe how you will apply appropriate ethical principles throughout the penetration testing process.

References

Deliverable 2: Reconnaissance Plan and Scanning Plan

Your second project deliverable will be due in Week 3. It will be two to four pages in length and will contain a Reconnaissance Plan and a Scanning Plan.

Reconnaissance Plan

In one to two pages, identify the specific passive and active methods you would use to gather key information about Haverbrook Investment Group as part of structured and ordered methodology. Provide one to two references in your plan.

As you are developing your reconnaissance plan, keep these questions in mind:

• As a malicious actor, how would you engage in a targeted attack against Haverbrook Investment Group while conducting passive reconnaissance techniques?
• What active reconnaissance techniques would you try?
• What techniques would you use for footprinting?
• How would you identify and explain the company’s presence on the internet?
• How would you find the company’s IP address range? How would you find the employees’ personally identifiable information (PII), such as email addresses and phone numbers?
• What potential impacts would your penetration testing techniques have on the confidentiality, integrity, and availability of the company’s private data as well as its networked systems?

Scanning Plan

In one to two pages, outline and discuss specific use cases to discover and enumerate information that could be used for potential exploitation. Some examples of information that you are gathering from Haverbrook Investment Group’s systems are usernames, machine names, shares, and services from a system. Identify any software, applications, or scripts that will be needed and provide a description of how this software will be used to gather information about Haverbrook’s systems.

As you are developing your scanning plan, keep these questions in mind:

• How would you detect active systems?
• How would you determine the best attack vector you wish to exploit?
• How would you prioritize different targets of opportunity?
• What tools would you be using for scanning and enumeration of systems and vulnerabilities?

Be sure to identify any needed software and provide a description of how it will be used to gather information about the systems.To assist in completing Deliverable 2, refer to Chapters 2, 3, and 4 in the textbook.

Use the same template from delivery one to finish your deliverable

Deliverable 3: Gaining Access Plan

After collecting enough information about the target during Deliverable 2 (Reconnaissance Plan and Scanning Plan), you will describe how to use that information to gain access to Haverbrook’s systems. Your one- to two-page plan on gaining access should include:

• details of the gaining access process in regards to the techniques commonly used to exploit low-privileged user accounts by cracking passwords through techniques such as brute-forcing, password guessing, and social engineering, and then escalating the account privileges to administrative levels in order to perform a protected operation.
• an implementation outline of any software that will be used in gaining access to the network(s) or system(s) You may include open source and commercial tools available to execute the actual exploit: Burp Suite, Cain and Abel, Core Impact, John the Ripper, Metasploit, and others. You can also use some programming languages, such as Javascript, Perl, Python, Ruby, or C++, if you choose to develop custom exploits.

As you are developing your Gaining Access Plan, keep these questions in mind:

• How would you escalate your privileges?
• How would you establish a command and control communication channel?

Refer to Chapter 6 in the textbook for the different techniques that can be used to gain access to the system.

Use the Gaining Access Template below to record your work

Penetration Test Proposal

Deliverable 3: Gaining Access Plan

Name:

Course Number and Section:

Instructor:

Date:

Gaining Access

Overview

Provide a summary of the Gaining Access phase.

Vulnerable Resources

Identify the resources where vulnerabilities can be located and include a brief description of those resources. Be sure to include a reference to the vulnerability, i.e., NVD.

Techniques and Software

Provide the techniques and any software, applications, or scripts that will be used in gaining access to the network(s) or system(s) along with a description of each technique. Refer to Chapter 6 in the textbook for additional information.

References

Deliverable 4: Maintaining Access Plan, Covering Your Tracks Plan, and Final Penetration Test Proposal

This deliverable includes three items:

• the last two parts of the Penetration Test Proposal (Maintaining Access and Covering Your Tracks)
• the entire final proposal with all previously submitted sections

Maintaining Access Plan

For this one- to two-page deliverable, identify the techniques you would use to maintain access to Haverbrook’s target network and/or system, as well as provide a brief summary of each technique. Include any software that is required to maintain access in the network or system(s).

As you are developing your Maintaining Access Plan, keep these questions in mind:

• Would you consider using a backdoor, a botnet, the reverse tunnel technique, polymorphic malware, or a toolkit as some examples to maintain access on the target network?
• What commercial tools would you use when pivoting to maintain and escalate control?
• How do you maintain access without causing damage to the system or network?
• How long do you stay in the system and/or network before the payload is released?

Covering Your Tracks

Some techniques attackers use to remain undetected are clearing the logs, updating firmware and using malicious programs such as backdoors or Trojans. Attackers also use tools such as Firmware Mod Kit, Firmalyzer Enterprise, and Firmware Analysis Toolkit to exploit firmware.

In one to two pages, provide a brief description of the methods, software tools, and any other means of avoiding detection and how each of these techniques would be used to hide your activities. To assist with completing Deliverable 4, refer to Chapter 6.

As you are developing your plans for maintaining access and covering your tracks, keep these questions in mind:

• What critical system files would be replaced to hide an attacker’s presence in the system?
• How would steganography or tunneling be used in an attacker’s efforts to conceal his or her presence?

Final Proposal

Add your previous submissions, make updates and corrections based on the feedback received from your instructor and add your Maintaining Access and Covering Your Tracks plan.

So, your final proposal will include the following components:

• Rules of Engagement (from Deliverable 1)
• Reconnaissance Plan (from Deliverable 2)
• Scanning Plan (from Deliverable 2)
• Gaining Access Plan (from Deliverable 3)
• Maintaining Access Plan (Deliverable 4)
• Covering Your Tracks Plan (Deliverable 4)

Use the format below to complete your final penetration test proposal

Penetration Test Proposal

Deliverable 4: Final Penetration Test Proposal

Name:

Course Number and Section:

Instructor:

Date:

Rules of Engagement

Overview

Include a brief description of the penetration test project.

Scope

Discuss the scope of the penetration test (pen test).

Checklist

Provide a list of the testing requirements.

Ethical Considerations

Describe how you will apply appropriate ethical principles throughout the penetration testing process.

Reconnaissance Plan

Overview

Provide a summary of the Reconnaissance phase.

Reconnaissance Methods

Identify specific methods and demonstrate a structured and ordered methodology while gathering key information that could be used to penetrate the network and systems of Haverbrook Investment Group. Discuss in detail both passive and active methods of reconnaissance.

Scanning Plan

Overview

Provide a summary of the Scanning phase.

Tactics, Techniques, and Procedures

Outline and discuss specific use cases to discover and enumerate information that could be used for potential exploitation. Some examples of information that you are gathering from Haverbrook Investment Group’s systems are usernames, machine names, shares, and services from a system. Identify any software, applications, or scripts that will be needed and provide a description of how this software will be used to gather information about Haverbrook’s systems.

Gaining Access Plan

Overview

Provide a summary of the Gaining Access phase.

Vulnerable Resources

Identify the resources where vulnerabilities can be located and include a brief description of those resources. Be sure to include a reference to the vulnerability, i.e., NVD.

Techniques and Software

Provide the techniques and any software, applications, or scriptsthat will be used in gaining access to the network(s) or system(s) along with a description of each technique. Refer to Chapter 6 in the textbook for additional information.

Maintaining Access Plan

Overview

Provide a summary of the Maintaining Access phase.

Techniques and Software

Identify the techniques used to maintain network and/or system access. Provide a brief summary of each technique. Include any software, applications, or scripts that may be needed to maintain access in the network or system(s). Refer to Chapter 6 in the textbook for additional information.

Covering Your Tracks Plan

Overview

Provide a summary of the Cover Your Tracks phase.

Techniques and Software

Identify the methods, software, applications, scripts and any other means of covering your tracks. Provide a brief description of how each of these will be used to hide from the system administrator. Refer to Chapter 6 in the textbook for additional information.

References