CompTIA Pentest + (PT0-002) Module 01 - Scoping Organizational/Customer Requirements

 

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PT0-002 / Module 01: Scoping Organizational/Customer Requirements for Penetration Testing

1. Introduction

Penetration Testing (PenTest) is a critical method for assessing and improving an organization’s cybersecurity posture. This chapter introduces the PenTest process, compliance requirements, and ways to maintain professionalism during the testing process.

Scoping Organizational/Customer Requirements for Penetration Testing is a crucial step in the process for several important reasons:

1. Defining Clear Objectives: Scoping helps establish clear, specific objectives for the penetration test. This ensures that the testing aligns with the organization’s security goals and addresses their most pressing concerns.

2. Resource Optimization: By clearly defining the scope, organizations can allocate resources more effectively. This prevents wasting time and effort on testing areas that are not critical or relevant to the organization’s security posture.

3. Risk Management: Proper scoping helps identify and prioritize the most critical assets and systems for testing. This ensures that high-risk areas receive appropriate attention and resources during the penetration test.

4. Legal and Compliance Considerations: Scoping helps ensure that the penetration test complies with relevant laws, regulations, and industry standards. It can help prevent unintended legal issues that might arise from testing beyond agreed boundaries.

5. Minimizing Operational Disruption: A well-defined scope can limit the potential for disruption to normal business operations. It can specify which systems can be tested, when testing can occur, and what types of tests are permissible.

6. Setting Expectations: Scoping sets clear expectations for both the testing team and the client. It helps prevent misunderstandings about what will be tested, how it will be tested, and what deliverables to expect.

7. Cost Control: By clearly defining the scope, organizations can better estimate and control the costs associated with penetration testing. It prevents scope creep and unexpected expenses.

8. Tailored Approach: Every organization has unique security needs. Scoping allows for a customized approach that addresses the specific requirements, concerns, and limitations of the organization.

9. Ethical Considerations: Proper scoping ensures that penetration testing is conducted ethically and responsibly. It sets boundaries that prevent testers from inadvertently accessing or compromising sensitive data or systems outside the agreed scope.

10.Measurable Outcomes: A well-defined scope allows for more measurable and comparable outcomes. This is particularly useful for tracking security improvements over time or comparing results across different penetration tests.

11.Regulatory Compliance: For industries subject to specific regulations (e.g., healthcare, finance), scoping ensures that penetration testing meets regulatory requirements and can be used as evidence of compliance.

12.Facilitating Communication: A clear scope provides a common understanding between all stakeholders, facilitating better communication throughout the penetration testing process.

13.Focusing on Business Context: Scoping allows the penetration test to be aligned with the organization’s business context, ensuring that the testing and results are relevant to the organization’s specific industry, size, and risk profile.

14.Preparing for Remediation: By clearly defining what will be tested, organizations can better prepare for potential findings and allocate resources for remediation efforts more effectively.

In conclusion, scoping Organizational/Customer Requirements for Penetration Testing is essential for ensuring that the testing is effective, efficient, relevant, and aligned with the organization’s needs and constraints. It sets the foundation for a successful penetration testing engagement that provides valuable insights and actionable results for improving the organization’s security posture.

1. Compare and contrast governance, risk, and compliance reports.

Explanation:

Governance reports focus on how an organization is managed and controlled. Risk reports identify and assess potential threats to an organization. Compliance reports demonstrate adherence to laws, regulations, and industry standards.

Illustrative Scenario:

A multinational bank, GlobalFinance, conducts annual assessments:

- Governance Report: Outlines the bank’s leadership structure, decision-making processes, and internal controls.

- Risk Report: Identifies potential cyber threats, market risks, and operational vulnerabilities.

- Compliance Report: Demonstrates adherence to regulations like GDPR, PCI DSS, and local banking laws.

While the governance report might recommend improving board oversight of cybersecurity, the risk report could highlight specific vulnerabilities in the online banking system. The compliance report would then show whether these vulnerabilities violate any regulatory requirements.

2. The importance of scoping and organizational/customer requirements

Explanation:

Scoping defines the boundaries of a penetration test, ensuring that testing efforts are focused, efficient, and align with the organization’s needs. Proper scoping prevents unnecessary work, reduces risks, and ensures that critical systems are thoroughly examined.

Illustrative Scenario:

TechInnovate, a software company, requests a penetration test for their new cloud-based application. The scoping process involves:

- Defining test boundaries (e.g., only the application, not the underlying cloud infrastructure)

- Identifying critical assets (e.g., user database, payment processing module)

- Setting test limitations (e.g., no denial of service attacks)

- Aligning with organizational requirements (e.g., testing during off-peak hours)

This scoping ensures that the penetration test focuses on TechInnovate’s most critical concerns while avoiding disruption to their business operations.

3. The importance of communication during the penetration testing process

Explanation:

Effective communication ensures that all stakeholders understand the test’s progress, findings, and implications. It helps manage expectations, allows for quick response to critical findings, and ensures that the final report meets the organization’s needs.

Illustrative Scenario:

During a penetration test for SecureHealth, a healthcare provider, the testing team discovers a critical vulnerability in the patient records system. They immediately communicate this to the client’s IT team, allowing for prompt mitigation. Throughout the test, they provide daily updates and a mid-test briefing, ensuring that SecureHealth’s management is fully informed and can make timely decisions about resource allocation and risk management.

4. Given a scenario, demonstrate an ethical hacking mindset by maintaining professionalism and integrity

Explanation:

An ethical hacking mindset involves conducting tests with permission, respecting boundaries, protecting sensitive data, and prioritizing the client’s security. It requires maintaining professionalism and integrity throughout the testing process.

Illustrative Scenario:

During a penetration test for EduOnline, an e-learning platform, the testing team gains access to a database containing student information. Instead of exfiltrating this data, they document the vulnerability, immediately inform the client, and provide recommendations for securing the database. They also ensure that all test data is securely deleted after the engagement, demonstrating their commitment to ethical practices and data protection.

5. Given a scenario, perform passive reconnaissance

Explanation:

Passive reconnaissance involves gathering information about a target without directly interacting with their systems. This can include using public sources, social media, and other openly available information.

Illustrative Scenario:

Before beginning an authorized penetration test for GreenEnergy, a renewable energy company, the testing team conducts passive reconnaissance:

- They analyze GreenEnergy’s website, noting technologies used and potential entry points.

- They review the company’s job postings to understand their technology stack.

- They examine public records and press releases for information about GreenEnergy’s infrastructure.

- They use OSINT tools to gather information about the company’s network ranges and email formats.

This passive reconnaissance provides valuable information for the subsequent phases of the penetration test, all without alerting GreenEnergy’s security systems or requiring any direct interaction with their network.

These objectives collectively ensure that penetration testers approach their work methodically, ethically, and in alignment with the client’s needs and regulatory requirements. They emphasize the importance of clear communication, professional conduct, and thorough preparation in the penetration testing process.

2. Defining Organizational PenTesting

2.1 Assessing Cyber Health and Resiliency

Organizations increasingly recognize the need to secure their systems. To ensure the Confidentiality, Integrity, and Availability (CIA) of data, many employ three main types of controls:

a) Administrative controls: These include policies and procedures. For example, password policies that require complex passwords and regular changes, or acceptable use policies that define how employees can use company resources.

b) Physical controls: These relate to protecting physical assets. Examples include locked server rooms, security cameras, and biometric access systems.

c) Technical or logical controls: These encompass software and hardware solutions such as firewalls, encryption, and intrusion detection systems.

All these controls should adhere to the Principle of Least Privilege, which means granting users only the minimum level of access rights they need to perform their jobs. This principle helps minimize the potential damage from accidents or malicious actions.

2.2 Reducing Overall Risk

A primary goal of PenTesting is to reduce overall risk. The formula for determining risk is:

RISK = THREAT * VULNERABILITY

Where:

- Threats can be malware, hackers, or even natural disasters.

- Vulnerabilities are weaknesses or flaws in the system that could be exploited.

For example, if a server has an unpatched vulnerability (scored 8 out of 10 in severity) and the threat of exploitation is moderate (5 out of 10), the risk would be 8 * 5 = 40 out of 100.

Risk management involves identifying, assessing, analyzing, and responding to these risks. PenTesting helps in this process by uncovering vulnerabilities before malicious actors can exploit them.

2.3 The CompTIA Structured PenTest Process

CompTIA outlines an eight-step process for conducting penetration tests:

1. Planning and scoping: This involves outlining the plan for the PenTest, including defining objectives, systems to be tested, and limitations.

2. Reconnaissance: Gathering information about the target. This can involve both passive (publicly available information) and active (direct interaction with the target) methods.

3. Scanning: Identifying live hosts, open ports, and running services. Tools like Nmap are often used in this phase.

4. Gaining access: Attempting to exploit vulnerabilities to see how deep into the network the tester can penetrate.

5. Maintaining access: Once access is gained, the tester tries to maintain it undetected for as long as possible, simulating a real attacker’s behavior.

6. Covering tracks: Removing any evidence of the penetration, such as log entries or created files.

7. Analysis: Analyzing the findings and deriving a summary of the risk rating for each vulnerability found.

8. Reporting: Delivering the results in a comprehensive report, often including an executive summary and detailed technical findings.

Scenario: PenTest of MediTech Healthcare Systems

MediTech is a regional healthcare provider with multiple clinics and a central hospital. They’ve hired CyberShield, a reputable cybersecurity firm, to conduct a comprehensive penetration test of their systems.

1. Planning and scoping: CyberShield meets with MediTech’s IT and management teams to outline the PenTest plan. They define objectives (assessing the security of patient records and the appointment system), systems to be tested (main hospital network, clinic networks, and patient portal), and limitations (no disruption to critical medical systems).

2. Reconnaissance: CyberShield begins gathering information about MediTech:

  • Passive: They search public records, analyze MediTech’s website, and review social media profiles of employees.
  • Active: They make phone calls to MediTech posing as potential patients to gather information about their systems.

3. Scanning: Using Nmap and other tools, CyberShield scans MediTech’s networks:

  • They identify live hosts across the hospital and clinic networks.
  • They discover open ports on various servers, including some unexpected open ports on the patient portal server.
  • They enumerate running services, noting an outdated version of a database service on one of the clinic servers.

4. Gaining access: CyberShield attempts to exploit the vulnerabilities found:

  • They use a known exploit for the outdated database service to gain initial access to a clinic server.
  • From there, they exploit a weak password on an administrator account to access the main hospital network.

5. Maintaining access: Once inside MediTech’s systems, CyberShield:

  • Creates a hidden user account with elevated privileges.
  • Installs a disguised remote access tool on several key servers.
  • Sets up scheduled tasks that periodically check in with their command and control server.

6. Covering tracks: To remain undetected, CyberShield:

  • Modifies system logs to remove evidence of their intrusion.
  • Deletes any temporary files created during their activities.
  • Ensures their remote access tool doesn’t appear in running processes lists.

7. Analysis: CyberShield analyzes their findings:

  • They identify critical vulnerabilities in the patient portal and clinic networks.
  • They assess the potential impact of each vulnerability, considering factors like ease of exploitation and potential data exposure.
  • They rate each vulnerability on a scale from low to critical based on their analysis.

8. Reporting: CyberShield delivers a comprehensive report to MediTech:

  • Executive Summary: High-level overview of the test, major findings, and overall risk assessment.
  • Detailed Technical Findings: In-depth explanation of each vulnerability, including how it was discovered and exploited.
  • Risk Ratings: Clear breakdown of risk levels for each vulnerability.
  • Recommendations: Specific, actionable steps for MediTech to address each vulnerability.
  • Appendices: Raw data from scans, screenshots of successful exploits (with sensitive information redacted), and other supporting evidence.

This scenario illustrates how each step of the penetration testing process is applied in a real-world context, demonstrating the methodical approach that professional pentesters take to thoroughly assess an organization’s security posture.

2.4 Comparing Steps Taken During PenTesting

It’s crucial to distinguish between PenTesting teams and actual threat actors:

- PenTesting Team: The main goal is to test an infrastructure’s defenses. They operate within agreed boundaries and with the organization’s permission.

- Threat Actor: The main goal is to alter the integrity of the system for malicious purposes. They have no boundaries and often aim to cause damage or steal information.

Understanding this difference helps in simulating real-world attacks while maintaining ethical and legal boundaries.

Scenario: SecureBank’s Online Banking Platform

SecureBank has recently upgraded its online banking platform and wants to ensure its security. They hire a PenTesting Team for a security assessment. Meanwhile, unknown to SecureBank, a Threat Actor group has also set their sights on the bank’s systems.

PenTesting Team:

1. Engagement: The team is officially hired by SecureBank and signs a contract outlining the scope and limitations of their work.

2. Objectives: Their goal is to identify vulnerabilities in the online banking platform to help SecureBank improve its security.

3. Methodology: They follow a structured approach, starting with reconnaissance and scanning, then attempting to exploit discovered vulnerabilities.

4. Limitations: They operate within agreed-upon boundaries. For example, they might avoid testing during peak hours to prevent disruption to customers.

5. Ethics: If they gain access to sensitive data, they do not exfiltrate or misuse it.

6. Communication: They maintain regular contact with SecureBank’s IT team, especially if they discover critical vulnerabilities.

7. Duration: Their engagement has a set timeframe, typically a few weeks.

8. Reporting: At the end of the test, they provide a detailed report of their findings and recommendations to SecureBank.

Threat Actor:

1. Engagement: They are not authorized and operate illegally, often from a remote location.

2. Objectives: Their goal is typically financial gain, either through stealing funds directly or selling stolen data on the dark web.

3. Methodology: While they might use similar tools and techniques as the PenTesting Team, they are not bound by any rules or ethics.

4. Limitations: They have no limitations and might attack at any time, including during peak hours to maximize confusion.

5. Ethics: If they gain access to sensitive data, they will exploit it for personal gain or sell it.

6. Communication: They avoid any communication with SecureBank, trying to remain undetected for as long as possible.

7. Duration: They may persist in the system for months or even years if undetected.

8. Reporting: Instead of a report, they might leave a ransom note if they decide to deploy ransomware, or simply disappear with the stolen data.

Example Outcome:

PenTesting Team: They discover a vulnerability in the password reset function that could allow account takeover. They immediately notify SecureBank, demonstrate the vulnerability in a controlled environment, and provide recommendations to fix it. SecureBank patches the vulnerability within days.

Threat Actor: They discover the same vulnerability but exploit it to gain access to multiple customer accounts. They transfer funds to untraceable accounts and sell customer data on the dark web. SecureBank only discovers the breach months later when customers report unauthorized transactions.

This example illustrates the stark contrast between PenTesting Teams and Threat Actors. While both may use similar techniques, their intentions, methods, and outcomes are fundamentally different. PenTesting Teams work to improve security with the organization’s knowledge and consent, while Threat Actors seek to exploit vulnerabilities for malicious purposes without the organization’s awareness.

3. Compliance Requirements

3.1 PCI DSS (Payment Card Industry Data Security Standard)

PCI DSS specifies controls that must be in place to handle credit card data. Key requirements include:

- Creating and maintaining a secure network infrastructure: This involves implementing firewalls and proper network segmentation.

- Protecting cardholder data: Using encryption for data transmission and storage.

- Maintaining a vulnerability management program: Regular updates and patches for systems.

- Implementing strong access control measures: Using multi-factor authentication and the principle of least privilege.

- Regularly monitoring and testing networks: Conducting regular security scans and penetration tests.

- Maintaining an information security policy: Documenting and enforcing security practices across the organization.

Companies must be vigilant in their efforts to secure data:

- They need to complete assessments and report the results.

- The merchant level defines whether they must complete a Report on Compliance (ROC).

- Level 1 merchants (processing over 6 million card transactions annually) must have an external audit performed by an approved Qualified Security Assessor (QSA).

- Levels 1 and 2 must complete a Report on Compliance.

- Levels 2–4 can either have an external auditor or submit a self-assessment questionnaire (SAQ) that proves they are taking active steps to secure the infrastructure.

3.2 General Data Protection Regulation (GDPR)

GDPR focuses on the privacy of consumer data:

- It affects anyone who does business with residents of the EU and Britain.

- Key components include:

a) Requiring consent: Organizations must ask permission for each data source they collect from individuals.

b) Allowing rescinding of consent: Consumers can opt out at any time.

c) Global reach: It applies to any organization handling EU residents’ data, regardless of where the organization is based.

d) Restricting data collection: Organizations should collect only what is necessary.

e) Violation reporting: Companies must report a breach within 72 hours of discovery.

3.3 Other Privacy Laws

- SHIELD Act (Stop Hacks and Improve Electronic Data Security): Enacted in New York state to protect citizens’ data. It requires businesses to implement safeguards for the “private information” of New York residents.

- California Consumer Privacy Act (CCPA): This law gives California residents more control over their personal information, including the right to know what data is being collected and the ability to request its deletion.

- Health Insurance Portability and Accountability Act (HIPAA): This U.S. law provides data privacy and security provisions for safeguarding medical information. It applies to healthcare providers, health plans, and healthcare clearinghouses.

Examples of companies or organizations that need to apply PCI DSS, GDPR, SHIELD Act, CCPA, and HIPAA, along with specific use cases and the benefits of compliance.

1. PCI DSS (Payment Card Industry Data Security Standard)

Example Organization: Global Retail Inc., an international e-commerce company

Use Case: Global Retail processes millions of credit card transactions annually through its online store and physical locations worldwide.

Application: They must implement PCI DSS standards across all their payment systems, including:

  • Encrypting cardholder data during transmission and storage
  • Regularly updating and patching systems
  • Implementing strong access controls
  • Conducting regular security assessments

Benefits:

  • Reduced risk of data breaches and associated costs
  • Increased customer trust and loyalty
  • Avoidance of hefty fines and penalties from card brands
  • Improved overall security posture

2. GDPR (General Data Protection Regulation)

Example Organization: EuroTech Solutions, a software company based in the US with customers in the EU

Use Case: EuroTech collects and processes personal data of EU citizens for its CRM and marketing activities.

Application: They need to:

  • Obtain explicit consent for data collection
  • Provide options for users to access, modify, or delete their data
  • Implement data protection measures
  • Appoint a Data Protection Officer

Benefits:

  • Enhanced trust with European customers and partners
  • Improved data management practices
  • Avoidance of severe GDPR fines (up to 4% of global annual turnover)
  • Competitive advantage in privacy-conscious markets

3. SHIELD Act (Stop Hacks and Improve Electronic Data Security Act)

Example Organization: NY Financial Advisors, a small financial consulting firm in New York

Use Case: The firm handles sensitive financial information of New York residents.

Application: They must:

  • Implement a data security program
  • Train employees on cybersecurity practices
  • Conduct regular risk assessments
  • Ensure third-party service providers can protect data

Benefits:

  • Reduced risk of data breaches
  • Improved customer confidence
  • Compliance with New York state law
  • Enhanced overall security practices

4. CCPA (California Consumer Privacy Act)

Example Organization: TechGiant Corp, a large technology company based in California

Use Case: TechGiant collects and processes personal information of California residents through its various online services.

Application: They need to:

  • Provide clear information about data collection practices
  • Offer opt-out options for data sales
  • Respond to consumer requests for data access or deletion
  • Implement reasonable security measures

Benefits:

  • Increased transparency and trust with California consumers
  • Improved data management and organization
  • Avoidance of CCPA penalties
  • Preparation for potential federal privacy laws

5. HIPAA (Health Insurance Portability and Accountability Act)

Example Organization: HealthCare Plus, a multi-state healthcare provider

Use Case: HealthCare Plus manages electronic health records and communicates with patients and other providers electronically.

Application: They must:

  • Implement strong access controls and authentication
  • Encrypt patient data in transit and at rest
  • Conduct regular security risk assessments
  • Train staff on privacy and security practices
  • Establish business associate agreements with vendors

Benefits:

  • Protection of sensitive patient information
  • Increased patient trust and satisfaction
  • Avoidance of severe HIPAA penalties
  • Improved operational efficiency through standardized practices

In all these cases, compliance not only helps organizations avoid penalties but also enhances their overall security posture, builds trust with customers, and often leads to improved operational practices. While the initial implementation can be challenging and potentially costly, the long-term benefits in terms of risk reduction and reputation enhancement typically outweigh the costs.

4. Comparing Standards and Methodologies

4.1 Identifying Pentesting Frameworks

Penetration Testing Frameworks are structured guidelines and methodologies that help security professionals conduct thorough and consistent security assessments. These frameworks provide a systematic approach to identifying vulnerabilities, exploiting weaknesses, and reporting findings in a standardized manner.

1. OWASP (Open Web Application Security Project)

OWASP is a non-profit foundation that works to improve the security of software. It provides various resources, tools, and methodologies for web application security.

Key components:

  • OWASP Top 10: A regularly updated list of the most critical web application security risks
  • OWASP Testing Guide: A comprehensive guide for testing web application security
  • OWASP ZAP (Zed Attack Proxy): An open-source web application security scanner

Example application: A financial technology startup is developing a new online banking platform. They use the OWASP Top 10 as a checklist to ensure they’re addressing the most critical security risks. During development, they regularly scan their application using OWASP ZAP to identify potential vulnerabilities. Before launch, they conduct a thorough assessment following the OWASP Testing Guide to ensure comprehensive security coverage.

2. NIST (National Institute of Standards and Technology)

NIST is a U.S. government agency that develops cybersecurity standards and guidelines. While not specifically a pentesting framework, NIST provides valuable resources for security testing.

Key components:

  • NIST SP 800–115: Technical Guide to Information Security Testing and Assessment
  • NIST Cybersecurity Framework: Provides a set of guidelines for mitigating organizational cybersecurity risks

Example application: A large government contractor is preparing for a security audit. They use NIST SP 800–115 to guide their internal security assessment process, ensuring they cover all aspects of their information systems. They also align their overall security strategy with the NIST Cybersecurity Framework, using its five core functions (Identify, Protect, Detect, Respond, Recover) to structure their security program.

3. OSSTMM (Open Source Security Testing Methodology Manual)

OSSTMM is a peer-reviewed methodology for performing security tests and metrics. It provides a scientific approach to testing the operational security of physical locations, human interactions, and all forms of communications.

Key components:

  • Six sections covering different types of security (Physical, Spectrum, Communications, Data Networks, Environmental, and Human)
  • RAV (Risk Assessment Values): A quantitative approach to measuring security

Example application: A multinational corporation wants to assess the security of its entire operation, including physical offices, digital infrastructure, and human factors. They use OSSTMM as a comprehensive framework for this assessment. For instance:

  • Physical security: They test access controls, surveillance systems, and alarm responses.
  • Data Networks: They conduct thorough network penetration tests.
  • Human: They perform social engineering tests to assess employee security awareness. After the assessment, they use OSSTMM’s RAV system to quantify their current security posture and track improvements over time.

Comparative Application of Frameworks:

Let’s consider a scenario where a large e-commerce company wants to conduct a comprehensive security assessment:

1. OWASP: They would use this primarily for their web applications and APIs. The security team would:

o Refer to the OWASP Top 10 to prioritize their testing efforts.

o Use the OWASP Testing Guide to ensure thorough coverage of web application security tests.

o Employ tools like OWASP ZAP for automated scanning.

2. NIST: The company would use NIST guidelines to ensure their overall security program is robust. They would:

o Follow NIST SP 800–115 for structuring their security testing process.

o Align their security strategy with the NIST Cybersecurity Framework, ensuring they have processes in place for all five core functions.

3. OSSTMM: This would be used for a more holistic security assessment. The team would:

o Assess physical security of their data centers using OSSTMM’s physical security section.

o Test network security using the data networks section.

o Conduct human factor assessments, including social engineering tests.

By combining these frameworks, the e-commerce company can ensure a comprehensive security assessment that covers web applications, overall cybersecurity posture, and specific technical and non-technical aspects of their operation.

In conclusion, while each of these frameworks has its strengths, they are often most effective when used in combination, allowing organizations to benefit from their complementary approaches to security assessment and improvement.

4.2 Providing Structure and Guidance

Structure and guidance in penetration testing refer to standardized frameworks and methodologies that provide a systematic approach to conducting security assessments. These frameworks offer several benefits:

1. Consistency: Ensures that all aspects of security are covered in each assessment.

2. Efficiency: Provides a roadmap for testers to follow, saving time and resources.

3. Comparability: Allows for meaningful comparisons between different assessments or over time.

4. Professionalism: Demonstrates a methodical approach to clients and stakeholders.

Let’s explore three prominent frameworks that provide structure and guidance in penetration testing:

1. ISSAF (Information Systems Security Assessment Framework)

ISSAF is an open-source framework developed by the Open Information Systems Security Group (OISSG).

Key features:

  • Comprehensive coverage of various security domains
  • Detailed methodology for each phase of penetration testing
  • Tools and techniques recommendations for each step

Structure: ISSAF is divided into three main phases:

1. Planning and Preparation

2. Assessment

3. Reporting, Clean-up, and Destruction of Artifacts

Practical Application: A large financial institution decides to conduct a comprehensive security assessment of its entire IT infrastructure. They choose ISSAF because of its thorough approach.

  • In the Planning and Preparation phase, they define the scope, gather information about their systems, and prepare testing tools.
  • During the Assessment phase, they follow ISSAF’s detailed guidelines for network mapping, vulnerability identification, and exploitation.
  • In the final phase, they compile a detailed report of their findings, clean up any changes made during testing, and ensure all sensitive data collected is securely destroyed.

2. PTES (Penetration Testing Execution Standard)

PTES provides a common language and scope for performing penetration testing.

Key features:

  • Seven main sections covering the entire penetration testing process
  • Technical guidelines for conducting tests
  • Emphasis on clear communication of findings

Structure:

1. Pre-engagement Interactions

2. Intelligence Gathering

3. Threat Modeling

4. Vulnerability Analysis

5. Exploitation

6. Post-Exploitation

7. Reporting

Practical Application: A mid-sized e-commerce company wants to test the security of its new payment processing system. They adopt PTES for this focused assessment.

  • In the Pre-engagement Interactions, they clearly define the scope, focusing specifically on the payment system.
  • During Intelligence Gathering and Threat Modeling, they identify potential attackers and their likely methods.
  • In Vulnerability Analysis and Exploitation, they discover and attempt to exploit weaknesses in the payment system.
  • Post-Exploitation involves seeing how far they can pivot from any initial access gained.
  • Finally, they produce a detailed report following PTES guidelines, clearly communicating the risks to both technical and non-technical stakeholders.

3. MITRE ATT&CK (Adversarial Tactics, Techniques, and Common Knowledge)

While not strictly a penetration testing framework, MITRE ATT&CK provides a comprehensive knowledge base of adversary tactics and techniques based on real-world observations.

Key features:

  • Detailed matrix of attacker tactics and techniques
  • Regular updates based on evolving threat landscape
  • Applicable to both offensive (red team) and defensive (blue team) operations

Structure: ATT&CK is organized into tactics (the “why” of an attack technique) and techniques (the “how”). It covers the entire attack lifecycle, including:

  • Initial Access
  • Execution
  • Persistence
  • Privilege Escalation
  • Defense Evasion
  • Credential Access
  • Discovery
  • Lateral Movement
  • Collection
  • Exfiltration
  • Command and Control

Practical Application: A government agency wants to improve its security posture against advanced persistent threats (APTs). They incorporate MITRE ATT&CK into their security testing and defense strategies.

  • Red Team: The penetration testing team uses ATT&CK to model their attacks, ensuring they’re using techniques employed by real-world adversaries. For example, they might use techniques listed under “Initial Access” like spearphishing or exploiting public-facing applications.
  • Blue Team: The defensive team uses ATT&CK to guide their detection and response strategies. They ensure they have controls and monitoring in place for each tactic and technique relevant to their environment.
  • Reporting: The red team’s findings are mapped to the ATT&CK matrix, showing which adversary techniques were successful and which were detected or prevented.
  • Improvement: Based on the results, the agency prioritizes security improvements, focusing on areas where multiple ATT&CK techniques were successful.

In conclusion, these frameworks provide essential structure and guidance for penetration testing, enabling more thorough, consistent, and effective security assessments. While each has its strengths, many organizations use a combination of frameworks to ensure comprehensive coverage of their security testing needs.

4.3 MITRE ATT&CK

MITRE ATT&CK (Adversarial Tactics, Techniques, and Common Knowledge)

MITRE ATT&CK is a globally-accessible knowledge base of adversary tactics and techniques based on real-world observations. It’s designed to be a comprehensive matrix of attacker behavior, providing a common language for the cybersecurity community.

Key Components:

1. Tactics: The “why” of an attacker’s action. These are the adversary’s tactical goals during an attack.

2. Techniques: The “how” of an attack. These are the specific methods used by adversaries to achieve their tactical goals.

3. Sub-techniques: More specific descriptions of adversary behavior than techniques.

4. Procedures: Specific implementations of techniques or sub-techniques used by adversaries.

ATT&CK Matrix: The ATT&CK Matrix organizes techniques into tactical categories:

1. Initial Access

2. Execution

3. Persistence

4. Privilege Escalation

5. Defense Evasion

6. Credential Access

7. Discovery

8. Lateral Movement

9. Collection

10.Command and Control

11.Exfiltration

12.Impact

Example Application:

Let’s consider a penetration testing scenario for a financial institution:

1. Initial Access: The pen-testers might use a spear-phishing attack (Technique T1566) to gain initial access.

2. Execution: Once they’ve gained access, they could use PowerShell (Technique T1059.001) to execute malicious code.

3. Privilege Escalation: They might exploit a vulnerability for privilege escalation (Technique T1068).

4. Discovery: The testers could use account discovery techniques (Technique T1087) to find high-value targets.

5. Lateral Movement: They might use remote services (Technique T1021) to move within the network.

6. Collection: The team could use data from local systems (Technique T1005) to gather sensitive information.

7. Exfiltration: Finally, they might exfiltrate data over an alternative protocol (Technique T1048) to simulate data theft.

Real-World Scenario:

In 2019, FireEye reported on an attack campaign targeting utilities sectors, which they dubbed “TEMP.Veles”. They used the MITRE ATT&CK framework to describe the adversary’s actions:

1. Initial Access: The attackers used spear-phishing emails with malicious attachments (Technique T1566.001).

2. Execution: They leveraged PowerShell scripts (Technique T1059.001) to run their malware.

3. Persistence: The adversaries created scheduled tasks (Technique T1053.005) to maintain access.

4. Privilege Escalation: They exploited vulnerabilities in unpatched systems (Technique T1068).

5. Defense Evasion: The attackers used obfuscated files (Technique T1027) to avoid detection.

6. Command and Control: They used custom C2 protocols (Technique T1094) for communication.

By mapping the attack to ATT&CK, FireEye provided a clear, standardized description of the threat actor’s behavior, which helped other organizations understand and defend against similar attacks.

MITRE ATT&CK and CALDERA:

CALDERA (Cyber Adversary Language and Operations Description for Red Team Automation) is an open-source automated adversary emulation system developed by MITRE. It uses the ATT&CK framework to perform adversary emulation operations.

The integration of ATT&CK and CALDERA allows for:

1. Automated Testing: CALDERA can automatically execute attack scenarios based on ATT&CK techniques.

2. Customizable Adversary Profiles: Security teams can create profiles that mimic specific threat actors or test particular attack chains.

3. Real-time Mapping: As CALDERA executes techniques, it maps them to the ATT&CK matrix in real-time.

4. Defensive Measurement: Organizations can use CALDERA to test their detection and response capabilities against ATT&CK techniques.

Example of combined usage:

A large corporation wants to test its defenses against a specific APT group. They would:

1. Use ATT&CK to identify the techniques commonly used by this APT group.

2. Create a custom adversary profile in CALDERA based on these techniques.

3. Run automated tests using CALDERA, which executes the techniques in a controlled manner.

4. Observe how their defense systems respond to each technique.

5. Use the results to improve their defenses, focusing on areas where detection or prevention failed.

This combination of ATT&CK’s comprehensive knowledge base and CALDERA’s automation capabilities provides a powerful tool for both offensive security testing and defensive improvement. It allows organizations to continually test and improve their security posture against real-world attack scenarios in a controlled, measurable way.

4.4 Investigating CVE and CWE

- CVE (Common Vulnerabilities and Exposures): A list of publicly disclosed cybersecurity vulnerabilities. Each entry includes an identification number, a description, and at least one public reference.

- CWE (Common Weakness Enumeration): A community-developed list of software and hardware weakness types. It serves as a common language for describing security weaknesses in architecture, design, or code.

5. Describing Ways to Maintain Professionalism

5.1 Validating the Team

Each member of a PenTesting team needs to prove they can work in a secure environment:

- Provide credentials: Such as relevant certifications (e.g., CompTIA PenTest+, CEH) that demonstrate appropriate skills for conducting PenTests.

- Produce recent background checks: These may include credit scores and driving records. It’s crucial to ensure no team member has a criminal record or felony conviction.

- Stress the importance of identifying and reporting criminal activity: Even if such activity is discovered accidentally during the course of testing.

5.2 Maintaining Confidentiality

- Everyone on the PenTest team must agree to conform to the policy on handling proprietary and sensitive information.

- The team should explicitly state to the client that the testers will protect any information they discover during testing.

5.3 Avoiding Prosecution

- Prior to beginning any testing, the team should outline the terms of the contract in detail.

- Review all possible legal considerations that might be applicable.

- Carefully think through all scenarios that might occur during testing.

- Step through how they will complete the testing, along with possible conflicts that might arise.

Conclusion

PenTesting is a crucial tool in assessing and improving an organization’s cybersecurity posture. By adhering to established processes, standards, and legal requirements, PenTest professionals can provide maximum value to their clients while maintaining the highest levels of professionalism and ethics.

This comprehensive guide covers the key aspects of penetration testing, from understanding the basics to maintaining professional standards. It provides a solid foundation for anyone looking to understand or conduct penetration tests in an organizational context.

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Example Scenario: E-commerce Company PenTest

Company Profile:

GlobalShop is a medium-sized e-commerce company that sells electronics worldwide. They process over 500,000 credit card transactions annually and store customer data including names, addresses, and purchase history.

Situation:

GlobalShop’s CEO has become increasingly concerned about cybersecurity after hearing about recent high-profile data breaches. The company decides to engage a professional penetration testing firm, SecureInsight, to assess their security posture.

PenTest Process:

1. Planning and Scoping:

SecureInsight meets with GlobalShop’s IT team to define the scope of the test. They agree to focus on the e-commerce platform, payment processing system, and customer database. They set a two-week timeframe for the test and establish rules of engagement, including a “do not test” list for critical production systems.

2. Reconnaissance:

The SecureInsight team begins by gathering publicly available information about GlobalShop. They find the company’s IP ranges, examine their website source code, and discover several employee email addresses through social media.

3. Scanning:

Using tools like Nmap, the team scans GlobalShop’s network, identifying open ports and services. They discover an outdated version of Apache running on the web server and several unpatched workstations.

4. Gaining Access:

Exploiting a known vulnerability in the outdated Apache version, the team gains initial access to the web server. From there, they use password spraying attacks with commonly used passwords and successfully access an administrator account.

5. Maintaining Access:

The team creates a backdoor on the compromised server and uses it to move laterally within the network, eventually gaining access to the customer database.

6. Covering Tracks:

The team carefully documents their actions and removes any artifacts they created during the test, such as temporary files or new user accounts.

7. Analysis:

SecureInsight analyzes their findings, identifying several critical vulnerabilities:

- Outdated server software

- Weak password policies

- Insufficient network segmentation

- Unencrypted customer data

8. Reporting:

The team prepares a comprehensive report, including:

- An executive summary for GlobalShop’s leadership

- Detailed technical findings

- Risk ratings for each vulnerability

- Recommendations for remediation

Compliance Implications:

- PCI DSS: The test reveals that GlobalShop is not fully compliant with PCI DSS requirements, particularly in areas of secure systems and encryption.

- GDPR: The discovery of unencrypted EU customer data indicates potential GDPR violations.

Professional Conduct:

Throughout the engagement, SecureInsight maintains strict confidentiality about their findings. They also ensure they operate within the agreed scope, stopping their test when they reach the customer database rather than attempting to exfiltrate data.

Outcome:

Based on SecureInsight’s report, GlobalShop implements several security improvements:

- Updating all server software

- Implementing stronger password policies and multi-factor authentication

- Improving network segmentation

- Encrypting all customer data

Six months later, GlobalShop engages SecureInsight for a follow-up test, which shows significant improvement in their security posture.

This scenario illustrates how penetration testing works in practice, covering the testing process, compliance considerations, and professional conduct. It shows how PenTesting can identify real vulnerabilities and lead to concrete improvements in an organization’s cybersecurity.

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