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A comprehensive, step-by-step penetration testing checklist for ethical hackers. Covers pre-engagement, information gathering, analysis, exploitation, reporting, and more. Ideal for both beginners and pros.

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Penetration Testing Guide & Checklist

Overview

A comprehensive guide for ethical penetration testing, meticulously designed to cover all phases of a penetration test. This step-by-step checklist ensures thorough coverage from preparation to reporting, ideal for both novice and experienced testers.


Table of Contents

  1. Pre-Engagement
  2. Information Gathering
  3. Vulnerability Analysis
  4. Exploitation
  5. Post-Exploitation
  6. Reporting
  7. Remediation Verification
  8. Specialized Testing Considerations
  9. Additional Resources
  10. Contributing

1. Pre-Engagement

Legal and Compliance

  • Secure a Non-Disclosure Agreement (NDA).
  • Obtain formal, written authorization for testing.
  • Ensure legal compliance with all relevant laws and regulations (e.g., GDPR, HIPAA).
  • Obtain appropriate insurance coverage (e.g., professional liability insurance).
  • Establish additional confidentiality agreements if necessary.

Scope Definition

  • Collect comprehensive client and system information.
  • Define the scope and rules of engagement clearly:
    • Identify in-scope and out-of-scope systems and applications.
    • Confirm any limitations or constraints (e.g., testing windows, sensitive systems).
  • Agree on acceptable testing methodologies and tools.
  • Establish safe testing periods to minimize business impact.
  • Identify third-party systems and obtain necessary permissions.

Communication and Planning

  • Set specific, measurable success criteria.
  • Establish emergency contact and response protocols.
  • Define data handling and storage protocols:
    • Agree on how sensitive data will be stored, transmitted, and destroyed.
  • Agree on communication channels and reporting frequency with the client:
    • Set up regular check-ins and progress updates.
  • Clarify testing schedule and time frame.
  • Ensure the penetration testing team has the necessary skills and certifications.

2. Information Gathering

Passive Reconnaissance

  • Perform WHOIS lookups and analyze domain registration information.
  • Conduct DNS analysis and enumerate subdomains.
  • Undertake passive information gathering (e.g., Shodan, Censys).
  • Utilize Open Source Intelligence (OSINT) techniques:
    • Gather information from social media, public forums, and past breaches.
    • Review job postings for insights into technologies and systems used.
    • Examine code repositories (e.g., GitHub) for exposed code or credentials.
  • Analyze SSL/TLS certificates for issuer details and expiration dates.
  • Perform Google dorking to find potentially sensitive information.

Active Reconnaissance

  • Conduct network and application scans (e.g., Nmap, Nessus).
  • Identify and enumerate all subdomains.
  • Perform web crawling for hidden or dynamic content.
  • Map network topology and identify network devices.
  • Identify technologies, platforms, and frameworks used in applications.
  • Search for common vulnerabilities (e.g., default credentials, unpatched systems).
  • Check for information leakage via metadata, HTML comments, etc.

Social Engineering Opportunities

  • Assess opportunities and methods for social engineering:
    • Monitor social media platforms for company-related disclosures.
    • Gather employee and organizational information from public sources.

3. Vulnerability Analysis

Automated Scanning

  • Validate and prioritize findings from automated scans.
  • Test for known vulnerabilities and possible exploits.
  • Use vulnerability assessment tools to identify potential issues.

Manual Testing

  • Analyze applications for common flaws:
    • SQL Injection (SQLi)
    • Cross-Site Scripting (XSS)
    • Cross-Site Request Forgery (CSRF)
    • Insecure Direct Object References (IDOR)
    • Insecure deserialization
  • Conduct fuzz testing to discover new vulnerabilities.
  • Review server and application configurations for misconfigurations.
  • Perform manual code reviews where feasible.
  • Assess authentication and authorization mechanisms.
  • Check for sensitive data exposure (e.g., in URLs, API responses).
  • Examine session management for weaknesses like session fixation.

Network and Infrastructure

  • Test for security misconfigurations in network devices (firewalls, routers).
  • Evaluate encryption and cryptographic practices, including SSL/TLS configurations.
  • Assess APIs for vulnerabilities such as improper authentication.
  • Assess logging and monitoring controls for effectiveness.
  • Examine third-party components and libraries for vulnerabilities.

Compliance and Standards

  • Verify adherence to industry standards (e.g., OWASP Top Ten, NIST).
  • Assess compliance with the organization's security policies and procedures.
  • Map findings to compliance requirements (e.g., PCI DSS, ISO 27001).

4. Exploitation

Initial Access

  • Attempt to gain initial access through:
    • Phishing campaigns (with explicit permission).
    • Exploiting known vulnerabilities.
    • Using default or weak credentials.
  • Utilize exploit frameworks (e.g., Metasploit) responsibly and within scope.

Privilege Escalation

  • Perform privilege escalation on compromised systems.
  • Exploit application logic flaws and business logic vulnerabilities.

Lateral Movement

  • Explore lateral movements within the network.
  • Attempt to access other systems and resources.

Security Evasion

  • Attempt to bypass security controls like WAF, 2FA, etc.
  • Try to evade detection by security solutions (e.g., antivirus, IDS/IPS).
  • Use custom or zero-day exploits cautiously and with explicit permission.

Documentation

  • Document each step of the exploitation process meticulously.
  • Maintain detailed logs of all actions for accountability and analysis.
  • Ensure all exploitation steps are reproducible and verifiable.

5. Post-Exploitation

Impact Analysis

  • Identify and access critical data stores.
  • Analyze the potential business and technical impacts of exploited vulnerabilities.
  • Evaluate the likelihood of real-world exploitation based on findings.

Persistence and Cleanup

  • Implement strategies for maintaining access, if necessary and authorized.
  • Remove all tools, scripts, and artifacts used during testing.
  • Ensure no backdoors, test accounts, or persistence mechanisms remain.
  • Verify that systems are restored to their pre-testing state.
  • Confirm that no sensitive data was altered or left exposed.

Data Handling

  • Adhere to secure data handling and processing procedures.
  • Check for clear-text credentials and sensitive data in memory.
  • Simulate data exfiltration, if within the agreed scope.

Documentation

  • Document all system alterations comprehensively.

6. Reporting

Report Preparation

  • Create a detailed technical report documenting tools, techniques, and procedures used.
  • Include evidence such as screenshots and logs.
  • Provide clear, actionable remediation recommendations.
  • Assign risk ratings to all identified vulnerabilities.
  • Follow industry-standard reporting formats (e.g., PTES, NIST guidelines).
  • Include a detailed methodology section explaining the testing approach.
  • Provide references to relevant industry standards and best practices.

Executive Summary

  • Prepare an executive summary for stakeholder review.
  • Include both technical details and high-level overviews for different audiences.

Classification and Security

  • Ensure the report is classified appropriately and sensitive data is secured.
  • Offer a prioritized action plan with clear timelines for remediation.

Client Communication

  • Conduct a read-out meeting with the client to discuss key findings.
  • Suggest a timeline for follow-up assessments or retesting.

7. Remediation Verification

Retesting

  • Allow a designated period for the client to remediate identified issues.
  • Conduct retests to verify the effectiveness of fixes.
  • Update the report with verification results and any new findings.
  • Validate that security controls are now functioning as intended.

Unresolved Issues

  • Document any unresolved security issues.
  • Recommend strategies for ongoing monitoring and improvement.

Continuous Improvement

  • Assist in identifying root causes to prevent future vulnerabilities.
  • Recommend improvements to policies, procedures, and security practices.
  • Propose integrating security into the software development lifecycle.
  • Advise on the need for security awareness and training programs.
  • Propose a schedule for regular future security audits.
  • Provide guidance on implementing a vulnerability management program.

8. Specialized Testing Considerations

IoT Device Testing

  • Firmware analysis for vulnerabilities.
  • Assess communication protocol security (e.g., MQTT, CoAP).
  • Perform hardware security testing (e.g., JTAG, UART interfaces).
  • Evaluate over-the-air (OTA) update security.
  • Check default configuration and hardcoded credentials.
  • Assess RF communication security (e.g., Bluetooth, Zigbee).
  • Review physical security controls.

Container Security

  • Analyze Docker security configurations.
  • Assess Kubernetes cluster security.
  • Perform container image scanning for vulnerabilities.
  • Implement runtime security monitoring.
  • Review service mesh configurations.
  • Evaluate container orchestration security.
  • Secure container registries.

CI/CD Pipeline Security

  • Secure source code management systems.
  • Assess build pipeline security.
  • Protect artifact repositories.
  • Secure deployment processes.
  • Evaluate Infrastructure as Code (IaC) security.
  • Implement secrets management best practices.
  • Enforce pipeline access controls.

Cloud Infrastructure

  • Conduct cloud configuration reviews.
  • Assess Identity and Access Management (IAM) policies.
  • Secure storage services (e.g., S3 buckets, Blob storage).
  • Review network security groups and firewall settings.
  • Evaluate serverless function security.
  • Test for misconfigurations in cloud environments.
  • Assess cloud-specific vulnerabilities and exploits.

9. Additional Resources


10. Contributing

We welcome and value contributions. Please feel free to submit pull requests or issues for improvements.

Contribution Guidelines

  • Ensure contributions align with industry standards and best practices.
  • Provide clear and concise descriptions of suggested changes.

Note: This checklist is intended for authorized penetration testing conducted with proper consent and in compliance with all applicable laws and regulations.


By following this comprehensive guide, penetration testers can ensure a thorough approach to security assessments, aligning with industry standards.

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A comprehensive, step-by-step penetration testing checklist for ethical hackers. Covers pre-engagement, information gathering, analysis, exploitation, reporting, and more. Ideal for both beginners and pros.

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