Rules of Engagement Penetration Testing:

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December 15, 2023

Engagement Penetration testing and ethical hacking are preventative techniques used to evaluate web systems by simulating real-world risks. These tests are performed in a controlled environment to uncover as many security flaws as feasible. This procedure is critical for providing useful input on how to successfully mitigate the risks associated with these vulnerabilities.

Many forward-thinking firms have included penetration testing, detailed vulnerability assessments, and meticulous source code analysis in their software development processes in response to expanding security concerns.

In response to growing security needs, many forward-thinking companies have integrated engagement penetration testing, comprehensive vulnerability assessments, and meticulous source code analysis into their software development processes.

. As a result, when they launch a new application, it has already undergone multiple phases of thorough testing and corrective measures.

There are critical aspects to consider before beginning a engagement penetration testing project, whether as a professional penetration tester for clients or as part of an internal security team within a business. These stages are critical for ensuring that the testing is both effective and consistent with the specific security objectives.

Guidelines for Conducting Engagement Penetration Testing

The Guidelines for Conducting Penetration Testing, commonly referred to as the Rules of Engagement (RoE), is an essential document outlining the specific procedures and protocols for carrying out a penetration test.

 This document is crucial in ensuring a structured and agreed-upon approach. Key elements that must be comprehensively detailed in the RoE before initiating the penetration test include:

  • 1. Detailed Testing Framework
  • 2. Contact Information of the Client
  • 3. Notification to the Client’s IT Team
  • 4. Management of Sensitive Information
  • 5. Regular Updates and Reporting Structure

Detailed Testing Framework

Penetration testing, an important security measure, is classified into three types: black box, white box, and hybrid gray box. The choice between these is determined by the engagement’s specific strategy and the degree of information available to the testing team.

Engagement Penetration Testing

Each form of testing has its own set of allowed and non-permissible actions. In black box testing, the team takes on the role of an external attacker who is unfamiliar with the company. They set out on a quest of exploration, aiming to map the network, comprehend deployed protection mechanisms, and investigate internet-facing websites and services, among other things.

This method, while mirroring the tactics of an external threat, should be weighed against potential inefficiencies. For instance, if the information the team seeks is already publicly accessible or if the hypothetical attacker is an informed insider, 

such as a disgruntled current or former employee, then investing in black box testing for internally-focused applications might not be the most resource-efficient strategy.

Conversely, white box testing encompasses a scenario where the team is armed with comprehensive knowledge about their targets. This can extend to having access to application source codes, thereby bypassing extensive reconnaissance and scanning activities. In this scenario, the focus is on deep analysis given the wealth of information at hand.

Sitting between these two is gray box testing, where the team is equipped with partial insights, such as application URLs, basic documentation, and user accounts. This approach is particularly beneficial for web application testing.

 The aim here is to unearth vulnerabilities within the application itself, rather than in the underlying server or network infrastructure. By utilizing user accounts, penetration testers can simulate the actions of a malicious user or an intruder who has infiltrated the system through social engineering tactics.

Each type of engagement penetration testing offers a unique lens through which to examine an organization’s security posture, tailored to specific contexts and objectives.

Contact Information of the Client

It is well acknowledged that, even when all necessary safety measures are implemented during testing procedures, there is always the chance of unforeseen complications due to the nature of these tests, which include pushing computer systems to their limits. This makes having correct and easily accessible contact information for clients critical for engagement penetration testing.

In the world of engagement penetration testing, there is always the possibility that these operations will accidentally lead to a Denial-of-Service (DoS) assault. To successfully address such problems,

Engagement Penetration Testing

 the client’s technical team must be accessible around the clock. This ensures prompt response and resolution, such as performing a hard reset, if a computer system becomes unresponsive and needs immediate attention to restore functionality.

Notifications for the Client’s IT Team

Penetration testing is used to analyze not only system vulnerabilities but also the effectiveness of support staff in dealing with issues and preventing intrusion attempts for penetration testing.

It is critical to communicate with the client to identify whether the test will be disclosed in advance or will come as a surprise. In circumstances when the test is pre-announced, it is critical to offer particular facts to the client, such as the exact timing and date of the test, as well as the originating IP addresses of the simulated attacks. 

This information is critical to avoid the client’s IT security team mistaking these test maneuvers for actual hostile attacks. If, on the other hand, the penetration test is to be carried out without prior warning,

it’s important to have a clear understanding with the client about the protocol to follow should the test be halted by either an automated defense mechanism or by the network administrator’s intervention for penetration testing.

Engagement Penetration Testing

The course of action, whether to cease testing or to proceed, hinges on the primary objective of the exercise: is it to evaluate the robustness of the infrastructure’s security, or is it to test the effectiveness of the network security and incident response team? 

Regardless of the nature of the test, it is vital to ensure that at least one individual within the escalation chain is informed about the timing and date of the test, even if the test is unannounced. Typically, web application penetration tests are pre-scheduled and communicated to the relevant parties.

Management of Sensitive Information for penetration testing:

During the testing team’s preparation and execution phases, they will have access to, and perhaps uncover, confidential information about the organization, its systems, and its users. 

The management of this sensitive information necessitates careful evaluation within the context of the Rules of Engagement (RoE). It is critical to put in place strong safeguarding and communication systems. 

These may include, but are not limited to, comprehensive disk encryption on tester workstations, emailed report encryption, and other security standards.

. Moreover, in scenarios where the client falls under the umbrella of stringent regulatory frameworks – such as the Health Insurance Portability and Accountability Act (HIPAA), the Gramm-Leach-Bliley Act (GLBA), or European data protection regulations – access to personal user data must be strictly confined to individuals who are officially authorized.

Regular Updates and Reporting Structure

Effective communication is the foundation of any successful penetration test. It is critical to establish regular touchpoints between the penetration testing team and the client’s organization to ensure clarity and progress. 

These sessions allow the testing team to deliver an update to the client on their progress, defining the scope of the penetration and highlighting any vulnerabilities discovered thus far..

Equally important is the client’s role in these discussions. They should provide feedback on their internal detection systems, specifically if any alarms were set off as a result of the engagement penetration testing activities. 

This is especially important for testing components like as web servers, especially when a Web Application Firewall (WAF) is in place. It is expected that the WAF will log and efficiently block any attempted breaches.

Another important aspect of these exchanges is the engagement penetration testing team’s record of test timings. This procedure is more than simply a formality; it is a key step that assists the client’s security team. 

The security team may more correctly identify and analyze the actions made during the test by synchronizing the penetration test chronology with their system logs. This interaction between the testing process and customer feedback is critical for a thorough and effective penetration testing.

Lucas Maes

Lucas Maes


Cybersecurity guru, encryption wizard, safeguarding data with 10+ yrs of IT defense expertise. Speaker & author on digital protection.

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