A penetration test, often shortened to pentest, can be performed using automated tools or manual methods. Each approach has unique advantages and limitations, making the choice between automated and manual pentesting a significant consideration for security teams. This post will address the pros and cons of both automated and manual penetration testing by describing some real-world examples to provide some insights into which method, or combination of methods, best suits your organization’s needs. Let’s first look at the pros and cons of each solution to see how they differ from one another.
Automated Penetration Testing
An automated penetration test involves specialized software that simulates cyberattacks, usually deploying scripts that search for known vulnerabilities.
Pros of automated penetration tests:
- Speed and efficiency. Automated tools can scan and analyze large systems quickly, covering extensive ground in a short time.
- Consistency. Automated tests follow predefined procedures and rules, ensuring consistent results.
- Cost effectiveness. Once purchased, automated tools can run multiple times with minimal additional costs, making them highly cost effective for regular scanning.
- Breadth of coverage. Automated tools can quickly identify known vulnerabilities across multiple systems and applications, ensuring broader coverage.
- Continuous Monitoring. Automated tools can be run at regular intervals, providing continuous monitoring and timely alerts about new vulnerabilities.
Cons of automated penetration tests:
- False positives and false negatives. Automated tools may generate false positives or miss certain vulnerabilities, and because they do not involve human intervention during testing, can lead to inaccurate assessments.
- Limited scope. Tools typically identify only known vulnerabilities and may not detect new or unknown threats.
- Lack of contextual understanding. Automated tools lack the contextual understanding to prioritize vulnerabilities based on factors like business impact. The tool is therefore ineffective at complex attack chains.
- Dependency on Tool Quality. The effectiveness of automated testing is highly dependent on the quality and currency of the tool.
Manual Penetration Testing
A manual penetration test involves a person, typically a cybersecurity expert, manually deploying simulated penetration techniques.
Pros of manual penetration tests:
- In-depth analysis. Human testers can perform more detailed and creative testing, identifying complex vulnerabilities that automated tools might miss.
- Contextual understanding. Manual testers can assess vulnerabilities in the context of the business environment, prioritizing them based on potential impact.
- Adaptability. Human testers can adapt their methods in real-time, exploring unexpected paths and scenarios.
- Exploit verification. Manual testing allows for the verification of vulnerabilities through real-world exploit attempts, ensuring that identified issues are genuinely exploitable.
Cons of manual penetration tests:
- Time-consuming. Manual testing is often slower than automated testing due to the detailed analysis required.
- Higher costs. Manual penetration testing typically involves higher costs due to the need for skilled professionals.
- Inconsistency. Results can vary depending on the expertise of the tester and the methodologies used, leading to potential inconsistencies.
- Limited scope for briefer assessments of large networks. For very large networks, manual testing within an affordable time period might not cover as much ground as automated testing within a reasonable timeframe.
Scenarios Where a Manual Pentest is the Best Option
While automated pentests cost less and require less person hours and expertise, they aren’t the best choice for every scenario. Automated solutions are usually not sophisticated enough to adequately test for complex attack chains with specific goals or focuses. One such engagement comes to mind where automated testing would not have achieved the goal of the pentest.
Our pentest team was given a specific flag to determine if we could gain access to an extremely sensitive and critical control system. The system was mostly segmented with access limited to a few employees. The attack chain started in typical way, with a phishing email and resulted in a compromised workstation. Next, we dumped the encrypted password hashes and the pentest team sent a series of active directory queries to determine who the engineers were and located their workstations. Again, nothing special here. Then we passed the hashes to the engineer workstations, which yielded administrative access to their systems. At this point, we could see that the lead engineer had access to the control system network but not the HMI (Human Machine Interface). We then scraped the file system for clues, and we found – you guessed it – a passwords.xls file. This file had passwords to the firewall within the control system network and our pentest team then logged into to the firewall and wrote a custom rule to give us access to the HMI. At this point, we thought we had won but we quickly realized we were wrong when we were prompted with a page requesting an access code that can only be issued by the support desk. We then called the support desk and impersonated a third party that was working on the control system. After a few minutes of arguing our case, they issued the unlock code and we obtained our flag.
Reflecting on this attack chain in perspective, there were multiple steps in the process where an automated pentest would not have succeeded. While some automated pentest platforms do include phishing, most that we’ve evaluated do not. Next, automated tests seldom seek out and target key personnel involved in a specific project. Finally, while an automated pentest might have discovered the password file, it wouldn’t know what to do with it and certainly never would’ve written the firewall rule to give itself access to a restricted network segment. If, by chance, an automated tool did manage to get through all of that, it would merely fingerprint the HMI without knowing how to proceed and would not have made the phone call for the needed information. It’s also important to note that while all of this was going on, vulnerability scans, network-based attacks, and additional attack paths were being discovered and exploited to help provide breadth to the assessment. AI is good but it’s not quite there, at least for now.
Scenarios where automated pentests make sense
Automated penetration testing is especially useful for large e-commerce platforms with dynamic infrastructures. These organizations, which often include multiple web applications, databases, APIs, and backend services across both on-premises and cloud environments, need to perform frequent vulnerability assessments. Integrating automated pentesting tools into their continuous integration and continuous deployment (CI/CD) processes allows for consistent security checks after every significant code change or deployment. This approach ensures quick identification of known vulnerabilities across all assets, maintaining a degree of security without manual intervention.
Automated tools provide the speed and efficiency needed in fast-paced environments, where delays in testing could hinder deployment processes. Additionally, the cost-effectiveness of automated tools—offering regular scans at a lower cost compared to hiring manual testers—makes them ideal for bridging the gap between annual manual pentests. These tools also guarantee consistent assessments by following predefined rules and procedures. Furthermore, automated pentesting helps maintain regulatory compliance by generating regular, documented security assessments and compliance-ready reports, simplifying the audit process.
In practice, an automated pentesting tool integrated into the CI/CD pipeline can scan updated components automatically whenever new code is pushed or new systems are deployed. Scheduled scans covering the entire infrastructure can run weekly or monthly, generating alerts for critical vulnerabilities and detailed reports for the security team to review. Once the development team addresses the identified issues, the automated tool rescans the affected components to verify remediation. This strategy ensures continuous, efficient, and cost-effective security assessments, maintaining a strong security posture in a dynamic and complex environment.
Hybrid penetration testing can be the best of both worlds
Finally, there is hybrid penetration testing, which leverages the strengths of both approaches by combining automated and manual penetration testing, creating an effective security assessment framework. In hybrid penetration testing, automated tools handle the regular, broad scans efficiently, identifying known vulnerabilities and ensuring continuous coverage. The automated testing then creates a baseline that allows human testers to focus their efforts on more complex, context-specific issues that require deeper investigation. The hybrid approach ensures that the testing addresses both surface-level and in-depth vulnerabilities, providing comprehensive security assessments. By using automated tools to identify and mitigate common vulnerabilities, and manual testing to uncover sophisticated threats, organizations can achieve a higher level of security resilience.
In practice, organizations can implement a hybrid approach by scheduling regular automated scans to maintain continuous monitoring and integrate these tools into their CI/CD pipelines for immediate vulnerability detection in new deployments. Concurrently, they can conduct periodic manual penetration tests, focusing on high-risk areas, critical applications, and emerging threats. This combination ensures that while the automated tools maintain a constant watch over the infrastructure, manual testers can provide detailed insights and expert analysis on more intricate security challenges.
Both automated and manual penetration testing have their unique strengths and weaknesses while a combination of both approaches often yields the best results. Automated tools can be used for regular, broad scans to quickly identify known vulnerabilities, while manual testing can delve deeper into specific areas, uncovering complex and context-specific issues. This hybrid approach ensures comprehensive security assessments, leveraging the efficiency of automation and the depth of human expertise.
How Tangible Security can help
Tangible Security offers a full range of penetration and security testing services including vulnerability assessments, penetration testing, cloud security assessments, ICS/OT security assessments, source code reviews, reverse engineering, social engineering testing, physical security, and red and purple team services. Our team of leading experts leverages both automated and manual approaches and applies an attacker’s mindset and innovative methodologies to uncover and help remediate security issues, vulnerabilities, misconfigurations, and process weaknesses.
Learn more: https://tangiblesecurity.com/penetration-and-security-testing/
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