Automated Pentesting Tools vs. Pentesting Experts

Penetration Testing

To protect ourselves from the attackers, it is crucial to evaluate our system, asset, or device from an attacker's perspective. The attacker's perspective means checking the target asset for all its loopholes, vulnerabilities, and possible backdoors as it can help an attacker succeed with their performed exploitation and access to the asset. Penetration testing gives an overall picture of vulnerabilities and security gaps in an IT infrastructure and directs towards mitigating possible cyber threats beforehand. It also trains the companies and their developers to secure the future development of their IT infrastructures, keeping in mind facing the potential threat landscape. Penetration testing/ vulnerability assessment is considered the initial cybersecurity strategy, which gives a broad picture of various adversarial strategies of getting initial access to a system during an attack.

Importance of Penetration Testing Expertise

Working of Automated Penetration Testing tools:

The first thing about these tools is that they are continuously improving, so what you might read here may be out of date after some time.

In these automated tools, penetration testing is performed by either an agent or through a Virtual Machine. As this process starts, the host system is simulated, and an attack proxy is established within the network. The penetration testing then goes into the implementation phase, starting from performing reconnaissance on the target environment. So, the automated tool focuses on the entire environment and conducts all vulnerability scanning techniques on all environment hosts. While in comparison, a human pentester decides the target within the environment instead of performing a penetration test on the entire environment. It also performs a vulnerability scan by choosing the tool/technique of its own choice.

In the second phase, the automated tool lists down the found vulnerabilities and potential vulnerabilities with their CVE references and CVSS scores and no references to how these can be exploited. They usually identify many false positives.

In the third phase, the automated tool decides which system, host, service, or vulnerabilities are best exploitable based on ease of exploitability, available exploitation script (from the list of scripts added in the automated tool). For example, if a Windows machine is detected, which is vulnerable to Eternal blue script vs. an open SSH port which requires performing brute forcing over its authentication. Then automated tool would choose the Eternal Blue script based on ease of exploitation.

Once the exploitation is performed successfully, the automated tool digs deeper into the target system/network. The automated tool starts the process from scratch, but before that, it forensically investigates the exploited system to gather more valuable information like password hashes, hardcoded credentials, or SSH keys. This additionally collected information is then added by the automated tool in its data set for use in the next round of expansion. For further propagation into the system, it will scan/exploit and try applying the hardcoded passwords, passing the hash attack or SSH port using the extracted key. If any of these gets successful, it further expands and starts the exploitation process from there and so on. In this whole process, it mimics the human actions by installing its agent on the exploited system part.

This entire discussion shows that automated tools are designed to mimic or follow a human pentester or attacker's behavior. But there are still some parts where it cannot mimic beyond a point, and that's where human pentester expertise role play comes in.

Penetration Testing Expert’s Pros Over Automated Pentest Tools

• Non-Understandability of Web Stacks/ Applications:

Unfortunately, the automated penetration testing tools cannot understand the web stack that is the web applications. When they detect a web application at some port or service level, they cannot further predict the vulnerability in it, e.g., IDOR vulnerability on an internal API, SSRF vulnerability on the internal webpage, XSS, and SQL injection. At the same time, all these can help to further dig into the system.

• Limitation to Internal Networks:

Automated penetration testing tools can work just inside the network, as most company's infrastructure have web-based applications, and these automated tools don't understand that. So, they are required to be brought inside the network by some human pentester as it performs outside the network pentesting and sets the automation tools inside the network.

What is Required of Penetration Testing Expertise?

• Knowledge of Vulnerabilities and Exploits Outside Automated Tool Suites:

There are also vulnerabilities discovered whose exploit codes are not yet available. So, when such a situation has been faced, the role of pentesting expertise comes in. When an automated tool cannot detect and exploit a vulnerability, we do not want to end up being helpless and getting our asset compromised. So, pentesters should know the existing and upcoming vulnerabilities landscape. They should be able to understand, modify and expand the current exploitation techniques to detect and tackle yet-to-be-known vulnerabilities.

• Continual of Seeking Knowledge:

Pentesters need to be in a continuous learning process. Learning it does not mean reading the writeup on the most remarkable exploits, but firing up the virtual machine by practically implementing and testing these codes. By implementation, it will help the pentesters build their expertise and come up with new exploits and so their defenses.

• Understanding of Secure Web Communications:

Testers need to understand secure web communication, from registering a web domain name to applying the domain name to a cloud-IP address to generate secure certificates for the domain. With this knowledge, a pentester can develop and teach such techniques into upcoming automated tool suites. 

Second comes the understanding of web technologies; pentesters need to know how these web applications are developed and works. Knowing web applications' constructors will make them identify input fields and gather the information that can potentially lead to future exploitation. So, when a pentester understands such things, he will be able to develop and tackle new upgraded exploitation attacks and up-gradation of automated tool suites accordingly.

• Ability to Write Scripts and Codes:

Pentesters need to have the ability to write code. So, they can explore new attacks, vulnerabilities, and their respective defenses because it is the pentester that will upgrade or amend the automated tool suites. 

Automated Penetration Testing Tools

Advantages:

• Faster and automated execution of vulnerability assessment and exploitation with corresponding report generation

• The automated vulnerability assessment process provides compliance to PCI-DSS pen-testing standards.

• With human pentesters, delivering the final reports takes so long that it becomes outdated. As the environment on which the test was conducted upgrades multiple times with the introduction of newer vulnerabilities and exploitations. Here comes the roleplay of automated tools, as they can run tests daily or under every change with delivering the upgraded reports.

• An automated tool can run penetration tests multiple times from different entry points to disclose vulnerable points in the network and develop various attack scenarios based on other entry points. Humans conducting such multiple entry point tests will require many human resource efforts with a colossal budget to pay for each conducted test and wait for getting the final generated reports.

Disadvantages:

• Automated penetration testing tools lack the experience and knowledge of years of work and studies.

• Most of the penetration testing tools can merely find the vulnerabilities that have been already reported.

• Automated tools cannot perform the process of gaining authority in the system by exploiting the two vulnerabilities together. A penetration tester’s experience is required for this process.

Automated Penetration Testing Tools can be useful for vulnerability analysis, but it is necessary not to be content with them. Penetration tests performed by penetration experts are always of great importance, and these manual tests are also critical for the accuracy of the test.

Use Cases of Automated Penetration Testing Tools:

• Assessing the Password Strength with available credential sniffing and password cracking exploits.

• Third-party assessment for gap analysis and remediation guidance.

• Testing Segmentation and Internal Firewalls by applying the available cyber intelligence Tactics, Techniques, and Procedures.

• Testing Active Directory loopholes and vulnerabilities.

• Testing Malware Injection and Detection.

• Testing security alerting of SIEM, EDR, and other solutions.

• Testing Critical Assets security posture validation.

• Detection of Rogue Assets.

• Detection of any default passwords on network devices.

• Testing security posture of IoT Devices.

• Validating existing security stack.

• Inculcating Improved Security Programmes.

Conclusion

Penetration testing is not a one-time test, but a test that should be done regularly. You do not know when the security vulnerabilities in your system will occur. As the Security for everyone team, we offer you all the necessary tests in a joint effort. You can contact for professional penetration testing service and ensure the security of your asset.