PENETRATION TESTing (PENTEST) - Deep Dive
Created by ChatGPT
What is a pentest?
A penetration test, often called a pentest, is a simulated cyberattack against a computer system, network, or application to identify and evaluate vulnerabilities that an attacker could exploit. The goal of a penetration test is to uncover security weaknesses before malicious actors do, allowing organizations to strengthen their defenses.
Key Features of Penetration Testing:
Simulates Real-World Attacks
Pen testers (ethical hackers) mimic the tactics, techniques, and procedures (TTPs) of real attackers to understand how systems react under attack.Identifies Vulnerabilities
Pen tests uncover weaknesses such as software bugs, misconfigurations, outdated systems, weak passwords, and insecure processes.Provides Insights for Improvement
The results help organizations prioritize and fix vulnerabilities to enhance their overall security posture.Ensures Compliance
Many industries require penetration testing to comply with standards like PCI DSS, HIPAA, or GDPR.Tests Incident Response
It evaluates how well an organization’s security team can detect, respond to, and mitigate a simulated attack.
Common Phases of a Penetration Test:
Planning and Reconnaissance
Understand the target system.
Gather information about the target (e.g., open ports, services, and users).
Scanning
Use tools to identify potential entry points or vulnerabilities in the target system.
Gaining Access
Attempt to exploit vulnerabilities to breach the system and gain access to its resources.
Maintaining Access
Simulate an attacker's effort to remain undetected within the system to demonstrate the potential for extended damage.
Analysis and Reporting
Compile a detailed report outlining discovered vulnerabilities, exploited weaknesses, and recommendations for remediation.
Types of Penetration Tests:
External Penetration Test: Focuses on assets exposed to the internet, such as websites and servers.
Internal Penetration Test: Simulates an attacker with access to the internal network.
Web Application Penetration Test: Targets web applications for vulnerabilities like SQL injection or cross-site scripting (XSS).
Wireless Penetration Test: Evaluates the security of Wi-Fi networks.
Social Engineering Test: Assesses an organization’s susceptibility to phishing or other manipulation tactics.
Physical Penetration Test: Tests physical security measures, like access to offices or data centers.
Penetration testing is an essential practice for proactive cybersecurity, helping organizations secure their systems and reduce the risk of breaches.
What are the methodologies of a pentest?
Penetration testing (pentesting) methodologies refer to the structured approaches and frameworks that guide how pentests are conducted. These methodologies ensure thorough, repeatable, and effective testing of systems and applications. Below are some of the key pentesting methodologies used in the industry:
OWASP (Open Web Application Security Project) Testing Guide
Purpose: Focused primarily on web applications, the OWASP methodology provides a comprehensive guide for testing security risks in web apps.
Key Areas: OWASP outlines common web vulnerabilities, such as cross-site scripting (XSS), SQL injection, and broken authentication. It covers everything from reconnaissance and information gathering to exploiting and reporting vulnerabilities.
Use Cases: Ideal for organizations seeking to secure their web applications, particularly e-commerce sites, SaaS products, or other internet-facing services.
NIST (National Institute of Standards and Technology) SP 800-115
Purpose: NIST SP 800-115 is a comprehensive methodology that provides guidelines for conducting technical information security testing, including pentesting.
Key Areas: The methodology covers several steps, including planning, information gathering, vulnerability analysis, exploiting vulnerabilities, and post-exploitation activities like reporting.
Use Cases: Popular in U.S. government and regulated industries (e.g., finance, healthcare) due to its detailed and standardized approach.
PTES (Penetration Testing Execution Standard)
Purpose: PTES is a collaborative effort designed to create a standard pentesting methodology that covers both technical and non-technical aspects of security testing.
Key Areas: PTES includes the pre-engagement phase (defining the scope), intelligence gathering, threat modeling, vulnerability analysis, exploitation, post-exploitation, and reporting.
Use Cases: This is a general framework that can be applied across different industries and is not limited to specific technologies or platforms.
OSSTMM (Open Source Security Testing Methodology Manual)
Purpose: OSSTMM provides a detailed methodology for testing operational security across networks, processes, physical systems, and human interactions.
Key Areas: OSSTMM breaks down security testing into different channels, such as physical security, wireless communications, data networks, and human security. It focuses on measuring and quantifying security risks.
Use Cases: Used for more comprehensive testing, including physical security testing or assessments of human factors (e.g., social engineering). It’s commonly employed in complex environments that require a multi-layered security approach.
ISSAF (Information Systems Security Assessment Framework)
Purpose: ISSAF provides a structured approach for security assessments, including pentesting. It integrates both technical testing and security policy assessments.
Key Areas: ISSAF covers areas such as reconnaissance, vulnerability identification, exploitation, and post-exploitation analysis, along with governance and compliance considerations.
Use Cases: Commonly used in organizations looking for a holistic security assessment framework, combining both technical vulnerabilities and security policies.
CREST (Council of Registered Ethical Security Testers)
Purpose: CREST provides a certification for pentesters and a standardized methodology for conducting penetration tests.
Key Areas: The CREST methodology focuses on various attack vectors such as network infrastructure, web applications, and wireless environments. It is highly structured, and all testing is carried out by certified professionals.
Use Cases: CREST is particularly popular in industries where certification and compliance are critical, such as finance, government, and healthcare.
Red Teaming Methodology
Purpose: Red teaming simulates real-world adversaries attempting to infiltrate an organization’s defenses, focusing not only on technology but also on people and processes.
Key Areas: Red team exercises focus on blending technical attacks (network, application, etc.) with social engineering, physical security breaches, and exploiting human factors. Unlike regular pentests, red teaming often goes beyond the predefined scope to simulate a real-world attack.
Use Cases: Typically used by larger organizations that want to assess their overall security posture in a holistic and adversarial manner.
TIBER-EU (Threat Intelligence-Based Ethical Red Teaming)
Purpose: TIBER-EU is a specific framework for financial institutions, developed by the European Central Bank. It focuses on using threat intelligence to simulate real-life cyberattack scenarios against financial infrastructures.
Key Areas: This methodology is intelligence-driven, meaning the tests are based on up-to-date threat data that mirrors actual attackers. The goal is to simulate the methods used by sophisticated cybercriminals targeting the financial sector.
Use Cases: Primarily used by European financial institutions looking to stress-test their resilience against advanced threat actors.
Selecting the right pentesting methodology depends on the specific needs of your organization, the scope of testing, and the industry in which you operate. While OWASP is widely known for web applications, methodologies like NIST, PTES, and OSSTMM offer broader frameworks that cover various layers of security. As cybersecurity threats continue to evolve, aligning with a robust and reputable pentesting methodology is crucial for identifying vulnerabilities and fortifying your organization’s defenses against potential attacks.
What are Rules of Engagement?
Rules of Engagement (RoE) refer to the predefined guidelines that outline the boundaries, scope, procedures, and acceptable practices during a penetration test (pentest). They are crucial in ensuring that the pentest is conducted in a safe, ethical, and controlled manner, balancing the need for rigorous testing with the protection of business operations, data, and systems.
RoE are established at the beginning of the pentesting process and agreed upon by both the pentesting team and the organization requesting the test. These guidelines ensure that everyone is aligned on the goals, risks, and limitations of the engagement.
Here’s a breakdown of what the RoE typically cover:
1. Scope of Testing
The RoE define exactly what is in-scope and out-of-scope for the test. This includes:
Systems: Which systems, networks, and applications will be tested.
Geography: If there are physical locations involved, which ones can be included.
Timeframe: The duration of the test, including the start and end dates.
By clarifying the scope, the pentesting team focuses only on the areas agreed upon, minimizing the risk of unexpected disruptions or security concerns.
2. Testing Boundaries
RoE set clear boundaries to ensure the test doesn't negatively impact business operations or cause unintended consequences. This includes:
Prohibited techniques: Certain high-risk techniques, such as Denial-of-Service (DoS) attacks, may be off-limits due to their potential to cause service disruptions.
Sensitive systems: Specific critical systems, such as production databases or financial systems, may be excluded from testing to prevent data loss or downtime.
These boundaries protect sensitive business functions and ensure the test doesn’t interfere with critical operations.
3. Legal and Ethical Considerations
RoE help ensure that the pentest is performed within legal and ethical guidelines. This may include:
Authorization: Legal permission from the organization to conduct the test and simulate attacks on their systems.
Ethical guidelines: Ensuring the pentesters do not exploit vulnerabilities beyond what is agreed upon, and that any sensitive data accessed is handled securely and responsibly.
This section ensures that both the organization and the pentesters are legally protected and that the test adheres to professional standards.
4. Risk Tolerance
Different organizations have varying levels of risk tolerance, and RoE allow for these differences to be addressed. This section may outline:
Risk levels: Whether the organization is willing to allow high-risk testing activities like privilege escalation or social engineering attacks.
Impact on business operations: Whether or not the pentesters are allowed to simulate attacks that could impact live systems.
The organization can set limits on how aggressive the pentesters can be to avoid unwanted business disruptions.
5. Communication Protocols
Effective communication is essential during a pentest to ensure that any issues are addressed promptly. RoE often include:
Who to notify: Points of contact within the organization and the pentesting team.
Communication channels: How and when the pentesters should report issues or findings, such as real-time notifications for critical vulnerabilities.
Emergency procedures: Protocols for halting the test if something goes wrong, such as a major system outage.
These guidelines ensure a smooth flow of information and quick responses to any unexpected incidents.
6. Reporting and Documentation
RoE outline what type of reporting is expected and how findings will be documented. This may include:
Interim reports: Regular updates on the status of the test.
Final report: A comprehensive document detailing vulnerabilities found, risk levels, and recommended remediation actions.
Post-test debrief: A meeting to discuss the findings and next steps for addressing vulnerabilities.
This ensures that the organization gets the information it needs in a clear, actionable format.
7. Post-Testing Activities
The RoE can also define what happens after the pentest is completed, such as:
Retesting: Whether the pentesting team will perform follow-up tests to ensure vulnerabilities have been fixed.
Remediation assistance: Whether the pentesters will assist with patching or fixing vulnerabilities.
Report delivery and debrief: How the results will be delivered and reviewed with stakeholders.
These post-engagement activities help ensure that the organization makes the most out of the pentest findings and improves its security.
Rules of Engagement are a critical component of any penetration testing engagement. They define the scope, boundaries, risks, and responsibilities, ensuring the test is conducted in a controlled, ethical, and legal manner. By establishing clear RoE, both the organization and the pentesting team can collaborate effectively, minimizing risks while gaining valuable insights into the security posture of the organization.
Pentest Resources
Podcasts
How to become a penetration tester - Part 1