Hack The Box

Structure of a Penetration Test

A penetration test employs a carefully structured, methodical process designed to systematically identify and document security vulnerabilities present within computer systems, network infrastructure, and applications. This well-organized approach enables security professionals to conduct their assessments with maximum efficiency, maintaining meticulous documentation throughout the testing process. Ultimately, pentesters provide their clients with detailed, actionable findings that clearly communicate both the discovered vulnerabilities and recommended remediation steps. While at this moment we will only cover the fundamental structure of a penetration test, we have also have a module called Penetration Testing Process that guides you through the complete process step-by-step.

1. Pre-Engagement Phase

The pre-engagement phase is crucial as it sets the foundation for the entire penetration test. During this phase, penetration testers work closely with the client to understand their specific needs, concerns, and objectives. This includes defining the scope of the test, establishing timelines, and determining which systems and networks will be tested.

Key documentation is created during this phase, including the Rules of Engagement (RoE) document, which outlines permitted testing activities, contact information for key personnel, and emergency procedures. Additionally, testers and clients sign necessary legal documents such as Non-Disclosure Agreements (NDAs) and service contracts to protect both parties.

2. Information Gathering Phase

Information gathering, also known as reconnaissance or intelligence gathering, involves collecting as much relevant information about the target as possible. This phase can be divided into passive and active reconnaissance.

Passive reconnaissance involves gathering information without directly interacting with the target systems. This might include analyzing public records, searching social media, reviewing company websites, and utilizing OSINT (Open Source Intelligence) tools. This approach leaves no trace and poses no risk to the target infrastructure.

Active reconnaissance, on the other hand, involves direct interaction with the target systems. This includes activities such as port scanning, service enumeration, and banner grabbing. While more intrusive, this provides detailed technical information about the target environment.

3. Vulnerability Assessment Phase

During the vulnerability assessment phase, penetration testers analyze the information gathered to identify potential security weaknesses. This involves using various automated scanning tools and manual testing techniques to discover vulnerabilities in systems, applications, and network infrastructure.

Importantly, this phase isn't just about running automated scanners. Skilled penetration testers must analyze the results, eliminate false positives, and understand how different vulnerabilities might be combined to create more significant security risks. This requires deep technical knowledge and experience in understanding how various systems and applications work.

4. Exploitation Phase

The exploitation phase is where penetration testers attempt to actively exploit the vulnerabilities identified in the previous phase. This is done to demonstrate the real-world impact of security weaknesses and to establish what an actual attacker might be able to achieve.

During exploitation, testers must carefully document their activities and maintain a precise record of the systems they've accessed. It's crucial to follow the agreed-upon Rules of Engagement and avoid causing any damage to production systems. Skilled testers often create detailed attack chains, showing how multiple vulnerabilities can be combined to achieve deeper access.

5. Post-Exploitation Phase

Once initial access is gained, the post-exploitation phase begins. This phase involves activities such as privilege escalation, lateral movement through the network, data exfiltration testing, and maintaining persistence. The goal is to understand the full extent of what an attacker could accomplish after breaching initial defenses.

Throughout this phase, testers must be particularly careful to document all their activities and maintain regular communication with the client's technical team. This helps ensure that any potential issues can be quickly addressed and that the testing doesn't inadvertently cause system outages or data loss.

6. Lateral Movement Phase

Lateral movement involves navigating through the network after gaining initial access to discover additional systems, resources, and potential targets. This phase focuses on identifying and exploiting trust relationships between systems and expanding the penetration tester's foothold within the network.

During lateral movement, testers employ various techniques such as credential harvesting, pass-the-hash attacks, and exploiting network protocols to move between systems. This phase helps demonstrate how an attacker could potentially spread through the organization's network infrastructure and access sensitive resources.

7. Proof of Concept

The proof of concept phase involves creating detailed documentation and evidence that demonstrates how vulnerabilities were exploited. This includes developing reliable and repeatable methods to reproduce the identified security issues, which helps validate the findings and assists the client's technical team in understanding and fixing the vulnerabilities.

At this phase, penetration testers create specific examples, scripts, or code that showcase the exploitation process. The resulting documentation typically includes step-by-step procedures, required tools or configurations, and any specific conditions necessary for the exploit to work. This information is crucial for both verifying the vulnerability and ensuring that the client's security team can effectively test their fixes.

8. Post-Engagement Phase

The reporting phase is critical as it transforms the technical findings into actionable information for the client. A well-written penetration testing report typically includes an executive summary for management, detailed technical findings for the IT team, and clear recommendations for remediation.

Each vulnerability should be clearly described, including its potential impact, steps to reproduce, and specific recommendations for fixing the issue. The report should also include evidence such as screenshots and logs to support the findings. Risk ratings should be assigned to help the client prioritize their remediation efforts.

9. Remediation Support and Retesting

After delivering the report, many penetration testing engagements include a period of remediation support. During this time, testers make themselves available to answer questions about their findings and provide additional guidance on implementing fixes.

Once the client has addressed the identified vulnerabilities, a retest is often performed to verify that the fixes were implemented correctly and that no new vulnerabilities were introduced during the remediation process. This helps ensure that the client's security posture has genuinely improved as a result of the penetration test.