Guide:  The Ultimate Pentest Checklist for Full-Stack Security

Pentest Checklists Are More Important Than Ever

Given the expanding attack surface coupled with the increasing sophistication of attacker tactics and techniques, penetration testing checklists have become essential for ensuring thorough assessments across an organization's attack surface, both internal and external. By providing a structured approach, these checklists help testers systematically uncover vulnerabilities in various assets like networks, applications, APIs, and systems. They ensure no critical area is overlooked and guide the testing process, making it more efficient and effective at identifying security weaknesses that could be exploited by attackers. A pentest checklist essentially leaves no stone unturned and is a detailed and comprehensive list of every type of vulnerability in which to simulate an attack against.

Each asset being tested, however, requires a different pentest checklist tailored to its specific characteristics and risks. For example, a checklist for pentesting web applications – which remains one of the top targets by malicious actors - will be quite lengthy but encompasses vulnerabilities that are unique to external-facing apps. These specialized checklists are a litmus test to ensure that security measures are evaluated, assesses for effectiveness, depending on the asset, and make overall testing more targeted and relevant to each environment.

BreachLock recently introduced a comprehensive guide that includes detailed pentest checklists of the primary stages involved in pentesting using various frameworks such as OWASP Top 10 and OWAS ASVS across every asset and all respective associated vulnerabilities for the following:

• Network – A pentest checklist for a Black Box external network testing including information gather, vulnerability scanning and enumeration, generic security findings, and service-based testing.
• Web Applications. A pentest checklist for Gray Box testing including user authentication, authorization testing, input testing, file-based attacks, error handling, business logic testing, and discovery and recon.
• APIs – A pentest checklist for Gray Box testing including user authentication, authorization testing, input testing, file-based attacks, error handling, business logic testing, and discovery and recon.
• Mobile - A pentest checklist for Gray Box testing including static analysis, dynamic analysis, and network analysis.
• Wireless – An abbreviated pentest checklist including identification of wireless network (SSID), unauthorized access to wireless networks, access security controls, and rogue access point detection
• Social Engineering- Aa abbreviated pentest checklist including phishing attacks, pretexting and impersonation, USB drops, and physical penetration.

This is a summary of why pentest checklists are important including an overview of a general pentest checklist. A complete guide for full-stack security, including BreachLock's compendium of comprehensive pentest checklists across all assets, can be accessed here.

Overview of Pentesting Delivery Models

Penetration testing has become one of the most effective offensive security measures to identify and assess vulnerabilities across both internal and external attack surfaces. Traditional pentesting methods have certainly evolved and penetration testing services are now widely used to help fortify an organization's security posture.

Pentesting is carried out by certified security experts who simulate real-world attacks to identify vulnerabilities for assessment and mitigation within a specific scope. These tests are based on detailed pentest checklists that are tailored by asset (e.g., web applications, network, APIs, etc.) and act as a guide for the pentest checklist process, ensuring standardized frameworks are used and testing adheres to applicable compliance requirements.

To better understanding pentesting, below are the varied methods used for penetration testing that lie in the delivery model, scalability, and frequency of testing, followed by pentest checklists by asset type.

Delivery Models

1. Traditional Penetration Testing: Typically performed manually by a team of certified pentesting experts over a fixed period (often a few days or weeks). The engagement is project-based with a final report delivered upon completion of testing.
   • Frequency: Usually performed on a periodic basis, such as annually or semi-annually, as part of compliance requirements or security audits.
   • Scalability: Limited in scalability due to the manual effort required by human testers and the one-off nature of the engagement.
   • Advantage: Deep analysis, thorough testing tailored to specific security requirements, and direct engagement with pentest experts.
   • Challenges: Fixed time frame and limited scope of assessment, which can leave gaps between tests.
2. Penetration Testing as a Service (PTaaS): PTaaS is a cloud-based model that offers ongoing penetration testing services, often integrated with platforms that provide real-time reporting and collaboration. It combines automated tools with human-led expertise.
   • Frequency: A more proactive approach that allows for continuous or more frequent approach to detecting and updating vulnerabilities as they emerge, .
   • Scalability: Highly scalable, as it leverages automation, cloud infrastructure, and hybrid models (automated testing with human validation), enabling rapid testing of multiple assets across different environments.
   • Advantage: Scalable, on-demand accessibility, hybrid efficiency, convenience, provides real-time insights, and allows for ongoing security testing.
3. Automated or Continuous Penetration Testing: Uses automation to continuously monitor and test systems for vulnerabilities and is often integrated with tools that run periodic scans.
   • Frequency: Provides ongoing or continuous assessments rather than periodic tests. Can be used for ongoing pentesting to validate security measure and/or to uncover new vulnerabilities as they emerge.
   • Scalability: Highly scalable, as it leverages automation enabling rapid testing of multiple assets across different environments.
   • Advantage: Efficient for frequent testing of repetitive tasks or enterprises in high computing environments, cost-effective, and ideal for covering large attack surfaces and complex IT infrastructures.
   • Challenges: Limited in identifying complex vulnerabilities and unique attack paths that require human intuition.
4. Human-led Penetration Testing: A manual and well-scoped process where certified pentest experts simulate realistic attack scenarios and TTPs, focusing on complex vulnerabilities that automated tools may miss.
   • Frequency: Relies on a human-driven approach whereby certified pentest experts explore potential attack vectors. Frequency is usually project-led and periodic.
   • Scalability: Highly customized to the enterprise's unique environment and assets. However, limited scalability due to the manual effort required by human testers
   • Advantage: In-depth analysis, greater flexibility, and a high success rate in discovering sophisticated vulnerabilities.
   • Challenges: Can be more time-consuming and costly than automated methods.

Pentest Checklists Across Your Attack Surfaces

High-Level Pentest Checklist

Creating a detailed pentest checklist is essential for performing thorough and effective security assessments. This first checklist is a general but expanded checklist that offers a structure approach to ensure both enterprises and CREST-certified pentest experts cover all critical areas in evaluating cybersecurity defenses.

1. Set Clear Objectives and Define Scope
   • Clarify Goals: Set concise objectives of the pentest engagement, such as identifying weaknesses for specific assets, compliance or security audit, or post-incident reconnaissance.
   • Define Scope: Specify the systems, networks, and applications that will be tested, including the type of testing (e.g., black box, white box, gray box) for each asset.
   • Establish Boundaries: Set parameters to avoid disrupting operations, such as not testing certain assets or limiting tests to outside business hours.
2. Assemble Penetration Testing Team
   • Build a Skilled Team: Include certified professionals with diverse expertise, such as network, application security, or social engineering specialists.
   • Check Credentials: Ensure pentest experts have relevant certifications like CREST, OSCP, OSWE, CEH, or CISSP, along with hands-on experience.
3. Obtain Necessary Approvals
   • Get Formal Authorization: Secure written consent from stakeholders detailing and agreeing upon scope, objectives, and limitations of the test to ensure legal compliance.
   • Document Process: Record all stages of the approval process, including discussions and any agreed-upon conditions. If using a third-party pentesting provider, the scope and process should be documented and signed off on.
4. Information Gathering
   • Analyze Targets: Gather comprehensive information about the infrastructure, including hardware, software, network design, and configurations.
   • Use OSINT: Apply open-source intelligence techniques to gather additional insights into the enterprise's online presence and potential weak points.
5. Generating a Pentest Roadmap
   • Attack Surface Management: Run automated scans using tools such as Nessus or OpenVAS to identify vulnerabilities, focusing on identifying issues without manual input to create a preliminary roadmap for penetration testing.
   • Validate Findings: Results from these scans can be validated to rule out false positives, understand the real context and impact of each potential vulnerability, and categorize by severity to provide a clear roadmap for penetration testing.
6. Create a Threat Model
   • Identify Potential Threats: Review recent attacks and TTPs, consider likely attackers - from random hackers to more targeted - likely attack paths, sophisticated entities, and their motivations.
   • Map Attack Vectors: Prioritize the possible ways an attacker could breach an enterprise based on its environment and the current threat landscape.
7. Simulate Attacks
   • Follow a Structure Approach: Conduct attacks systematically, attempting to exploit weaknesses, bypass controls, and gain higher privileges where possible.
   • Adhere to Ethical Standards: Ensure testing is conducted by certified experts, following standardized frameworks and compliance standards, to minimize risks to systems and data.
8. Gather Data and Analyze Results
   • Capture Evidence: Collect thorough evidence for each attack, such as proof of concepts (POCs) via screenshots, potential attack paths for each domain and associated subdomains and IPs.
   • Assess Impact: Evaluate the consequences or impact of each vulnerability, including potential data breaches, system compromise, and operational disruption and prioritize findings by risk severity and potential impact.
9. Prepare and Deliver Reports
   • Document Findings: Provide a detailed report on each vulnerability and technical descriptions, POCs, risk severity, potential impact, and remediation recommendations.
   • Prioritization: Penetration testing or PTaaS providers will work with enterprises to rank vulnerabilities based on risk and develop a plan for remediation in line with available resources.
10. Support Remediation Efforts
    • Actionable Mitigation: Present clear recommendations on how to mitigate each issue based on severity and impact.
    • Retesting: Verify effectiveness of remediation by conducting follow-up pentest to ensure issues have been resolved.
11. Communicate with Stakeholders
    • Present Results: Share findings by providing story of impact if no action is taken. This is a much more effective strategy then providing a laundry list of vulnerabilities. Summarize key risks and actions for non-technical stakeholders.
    • Foster Dialogue: Engage in discussions to address any concerns or questions about reporting and remediation efforts.

Conclusion

Pentest checklists serve pentest experts and their organizations by ensuring a consistent, comprehensive, and systematic approach to identifying security vulnerabilities. A pentest checklist leaves no stone unturned and facilitates better communication between pentesters and stakeholders. They provide a clear outline of what will be tested, evaluated, and how the findings will be assessed. This transparency helps enterprises understand their security posture and to make more informed decisions about improvements.

Pentest checklists are not only effective in identifying vulnerabilities but ensure a systematic approach, using the best practices, tools, and frameworks, for penetration testing. They benefit pentesters by providing assurances to their organization and stakeholders that they are taking meaningful steps to protect their assets. Pentest checklists are a security blanket for any organization conducting penetration testing as a Service.

For more detailed pentest checklists, click here for the complete guide for full-stack security, including BreachLock's compendium of comprehensive pentest checklists across all assets.