BackTrack 4: Target Scoping

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BackTrack 4: Assuring Security by Penetration Testing

BackTrack 4: Assuring Security by Penetration Testing

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Target Scoping is defined as an empirical process for gathering target assessment requirements and characterizing each of its parameters to generate a test plan, limitations, business objectives, and time schedule. This process plays an important role in defining clear objectives towards any kind of security assessment. By determining these key objectives one can easily draw a practical roadmap of what will be tested, how it should be tested, what resources will be allocated, what limitations will be applied, what business objectives will be achieved, and how the test project will be planned and scheduled. Thus, we have combined all of these elements and presented them in a formalized scope process to achieve the required goal. Following are the key concepts which will be discussed in this article:

  • Gathering client requirements deals with accumulating information about the target environment through verbal or written communication.
  • Preparing test plan depends on different sets of variables. These may include shaping the actual requirements into structured testing process, legal agreements, cost analysis, and resource allocation.
  • Profiling test boundaries determines the limitations associated with the penetration testing assignment. These can be a limitation of technology, knowledge, or a formal restriction on the client’s IT environment.
  • Defining business objectives is a process of aligning business view with technical objectives of the penetration testing program.
  • Project management and scheduling directs every other step of the penetration testing process with a proper timeline for test execution. This can be achieved by using a number of advanced project management tools.

It is highly recommended to follow the scope process in order to ensure test consistency and greater probability of success. Additionally, this process can also be adjusted according to the given situation and test factors. Without using any such process, there will be a greater chance of failure, as the requirements gathered will have no proper definitions and procedures to follow. This can lead the whole penetration testing project into danger and may result in unexpected business interruption. Paying special attention at this stage to the penetration testing process would make an excellent contribution towards the rest of the test phases and clear the perspectives of both technical and management areas. The key is to acquire as much information beforehand as possible from the client to formulate a strategic path that reflects multiple aspects of penetration testing. These may include negotiable legal terms, contractual agreement, resource allocation, test limitations, core competencies, infrastructure information, timescales, and rules of engagement. As a part of best practices, the scope process addresses each of the attributes necessary to kickstart our penetration testing project in a professional manner.

As we can see in the preceding screenshot, each step constitutes unique information that is aligned in a logical order to pursue the test execution successfully. Remember, the more information that is gathered and managed properly, the easier it will be for both the client and the penetration testing consultant to further understand the process of testing. This also governs any legal matters to be resolved at an early stage. Hence, we will explain each of these steps in more detail in the following section.

Gathering client requirements

This step provides a generic guideline that can be drawn in the form of a questionnaire to devise all information about target infrastructure from a client. A client can be any subject who is legally and commercially bounded to the target organization. Such that, it is critical for the success of the penetration testing project to identify all internal and external stakeholders at an early stage of a project and analyze their levels of interest, expectations, importance, and influence. A strategy can then be developed for approaching each stakeholder with their requirements and involvement in the penetration testing project to maximize positive influences and mitigate potential negative impacts. It is solely the duty of the penetration tester to verify the identity of the contracting party before taking any further steps.

The basic purpose of gathering client requirements is to open a true and authentic channel by which the pentester can obtain any information that may be necessary for the testing process. Once the test requirements have been identified, they should be validated by a client in order to remove any misleading information. This will ensure that the developed test plan is consistent and complete.

We have listed some of the commonly asked questions that can be used in a conventional customer requirements form and the deliverables assessment form. It is important to note that this list can be extended or shortened according to the goal of a client and that the client must retain enough knowledge about the target environment.

Customer requirements form

  1. Collecting company’s information such as company name, address, website, contact person details, e-mail address, and telephone number.
  2. What are your key objectives behind the penetration testing project?
  3. Determining the penetration test type (with or without specific criteria):
    • Black-box testing or external testing
    • White-box testing or internal testing
    • Informed testing
    • Uninformed testing
    • Social engineering included
    • Social engineering excluded
    • Investigate employees background information
    • Adopt employee’s fake identity
    • Denial of Service included
    • Denial of Service excluded
    • Penetrate business partner systems
  4. How many servers, workstations, and network devices need to be tested?
  5. What operating system technologies are supported by your infrastructure?
  6. Which network devices need to be tested? Firewalls, routers, switches, modems, load balancers, IDS, IPS, or any other appliance?
  7. Is there any disaster recovery plan in place? If yes, who is managing it?
  8. Are there any security administrators currently managing your network?
  9. Is there any specific requirement to comply with industry standards? If yes, please list them.
  10. Who will be the point of contact for this project?
  11. What is the timeline allocated for this project? In weeks or days.
  12. What is your budget for this project?
  13. List any other requirements as necessary.

Deliverables assessment form

  1. What types of reports are expected?
    • Executive reports
    • Technical assessment reports
    • Developer reports
  2. In which format do you want the report to be delivered? PDF, HTML, or DOC.
  3. How should the report be submitted? E-mail or printed.
  4. Who is responsible for receiving these reports?
    • Employee
    • Shareholder
    • Stakeholder

By using such a concise and comprehensive inquiry form, you can easily extract the customer requirements and fulfill the test plan accordingly.

Preparing the test plan

As the requirements have been gathered and verified by a client, it is now time to draw a formal test plan that should reflect all of these requirements, in addition to other necessary information on legal and commercial grounds of the testing process. The key variables involved in preparing a test plan are a structured testing process, resource allocation, cost analysis, non-disclosure agreement, penetration testing contract, and rules of engagement. Each of these areas will be addressed with their short descriptions below:

  • Structured testing process: After analyzing the details provided by our customer, it may be important to re-structure the BackTrack testing methodology. For instance, if the social engineering service was excluded then we would have to remove it from our formal testing process. This practice is sometimes known as Test Process Validation. It is a repetitive task that has to be visited whenever there is a change in client requirements. If there are any unnecessary steps involved during the test execution then it may result in a violation of the organization’s policies and incur serious penalties. Additionally, based on the test type there would be a number of changes to the test process. Such that, white-box testing does not require information gathering and target discovery phase because the auditor is already aware of the internal infrastructure.
  • Resource allocation: Determining the expertise knowledge required to achieve completeness of a test is one of the substantial areas. Thus, assigning a skilled penetration tester for a certain task may result in better security assessment. For instance, an application penetration testing requires a dedicated application security tester. This activity plays a significant role in the success of penetration testing assignment.
  • Cost analysis: The cost for penetration testing depends on several factors. This may involve the number of days allocated to fulfill the scope of a project, additional service requirements such as social engineering and physical security assessment, and the expertise knowledge required to assess the specific technology. From the industry viewpoint, this should combine a qualitative and quantitative value.
  • Non-disclosure Agreement (NDA): Before starting the test process it is necessary to sign the agreement which may reflect the interests of both parties “client” and “penetration tester”. Using such a mutual non-disclosure agreement should clear the terms and conditions under which the test should be aligned. It is important for the penetration tester to comply with these terms throughout the test process. Violating any single term of agreement can result in serious penalties or permanent exemption from the job.
  • Penetration testing contract: There is always a need for a legal contract which will reflect all the technical matters between the “client” and “penetration tester”. This is where the penetration testing contract comes in. The basic information inside such contracts focus on what testing services are being offered, what their main objectives are, how they will be conducted, payment declaration, and maintaining the confidentiality of a whole project.
  • Rules of engagement: The process of penetration testing can be invasive and requires clear understanding of what the assessment demands, what support will be provided by the client, and what type of potential impact or effect each assessment technique may have. Moreover, the tools used in the penetration testing processes should clearly state their purpose so that the tester can use them accordingly. The rules of engagement define all of these statements in a more detailed fashion to address the necessity of technical criteria that should be followed during the test execution.

By preparing each of these subparts of the test plan, you can ensure the consistent view of a penetration testing process. This will provide a penetration tester with more specific assessment details that has been processed from the client requirements. It is always recommended to prepare a test plan checklist which can be used to verify the assessment criteria and its underlying terms with the contracting party. One of such exemplary types of checklist is discussed in the following section.

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