Automated Penetration Testing

Automated Penetration Testing

Article by Tsaaro

7 min read

Automated Penetration Testing


Penetration testing is the process of simulating real cyber-attacks against your own systems in order to discover security holes that attackers can take advantage of. It’s a term that encompasses the many types of security testing that can be used to help protect against malicious actors wishing to compromise your systems or sensitive information. Penetration testing checks your systems for vulnerabilities which include web-layer security problems (such as SQL injection and cross-site scripting), infrastructure weaknesses (such as remote code execution flaws), and other security misconfigurations (such as weak encryption configurations, and systems that are unnecessarily exposed).

Methodology for conducting pentests

Generally, testing engineers perform the following methods:

  1. Data Collection − Data collection plays a key role in testing. One can either collect data manually or can use tool services (such as webpage source code analysis technique, etc.) freely available online. These tools help to collect information like table names, DB versions, database, software, hardware, or even about different third party plugins, etc
  2. Vulnerability Assessment − Once the data is collected, it helps the testers to identify the security weakness and take preventive steps accordingly.
  3. Actual Exploit − This is a typical method that an expert tester uses to launch an attack on a target system and likewise, reduces the risk of attack.
  4. Report Preparation − Once the penetration is done, the tester prepares a final report that describes everything about the system. Finally the report is analyzed to take corrective steps to protect the target system.

Need for automating Penetration Testing

Manual penetration testing is a great way to take a snapshot of your security at a point in time. However, modern attackers are automating their efforts, scanning the internet constantly for vulnerabilities to exploit, and businesses can no longer afford not to have their own automated penetration testing tools in place.

Reconnaissance and attack surface exploration were mostly conducted by a multitude of self-developed tools in C or Perl, actively discussed on many dedicated IRC channels. Google Dorking and Shodan have not yet existed, and the entire process of penetration testing was quite laborious, unscalable and time-consuming. Dynamic web applications were at the very nascent stage of their proliferation, while fairly trivial buffer overflow vulnerabilities and their variations affected countless network services, including omnipresent FTP, OpenSSL, SSH and web servers, and required quite advanced technical skills to get exploited. Most of the exploits purported to take control over the remote server required a quite advanced knowledge of C and assembly programming languages, computer memory management and shell coding (creation of exploit payload, usually executing a Unix command line a.k.a. “shell”).

Hence, industry professionals and security enthusiasts were continuously trying to bring automation into all steps of manual penetration testing to accelerate the process, reduce costs and provide better value for money. Many simple but efficient penetration testing tools like Nikto or Hydra were getting skyrocketing popularity to automate such trivial tasks as web server stack enumeration or remote password brute-forcing. Eventually, Kali Linux and Metasploit paved the road to the commencement of automated penetration testing that, however, always required an experienced ethical hacker commanding and orchestrating a portfolio of automated security tools.

What is Automated Penetration Testing?

Automated penetration testing is much faster, efficient, easy, and reliable that tests the vulnerability and risk of a machine automatically. This technology does not require any expert engineer, rather it can be run by any person having the least knowledge of this field. Tools for automated penetration testing are Nessus, Metasploit, OpenVAs, backtract (series 5), etc. These are very efficient tools that changed the efficiency and meaning of penetration testing.

Automated penetration testing services and SaaS solutions incrementally substitute traditional human-driven penetration testing, providing greater scalability, efficiency and effectiveness with DevSecOps integrations if implemented and conducted correctly.

The following table illustrates the fundamental difference between the manual and automated penetration testing −

Manual Penetration TestingAutomated Penetration Testing
It requires an expert engineer to perform the test.It is automated so even a learner can run the test.
It requires different tools for the testing.It has integrated tools that require anything from outside.
In this type of testing, results can vary from test to test.It has fixed results.
This test requires remembering to clean up memory by the tester.It does not.
It is exhaustive and time taking.It is more efficient and fast.
It has additional advantages i.e. if an expert does pen test, then he can analyze better, he can think what a hacker can think and where he can attack. Hence, he can put security accordingly.It cannot analyze the situation.
As per the requirement, an expert can run multiple testing.It cannot.
For critical conditions, it is more reliable.It is not.

Artificial Intelligence and Machine Learning for Automated Penetration Testing

Automation is a key to success and will probably remain a hot topic within the next decade. Being mindful of this, automated pentests leverage Machine Learning, including Deep Learning Artificial Neural Networks (ANN) for intelligent automation and acceleration of a wide spectrum of penetration testing tasks and processes.
This is not only scalable but also cost efficient.

While we cannot fully automate the integrity of a skillful penetration testing labor, we can effectively reduce human time required to conduct advanced testing of OWASP Top 10 vulnerabilities, covering such exploitation vectors and attacking techniques that automated scanning software is flatly unable to perform with their traditional algorithms.

How to select an Automated Penetration Testing company?

A hallmark of a penetration test is an actionable report free from false positives. This perfectly applies both for human-driven and automated penetration testing. Thus, if a vendor is unable to provide you with a contractual guarantee that in the report you won’t have false positives, their offering is not about penetration testing. Another aspect to consider is some advanced testing capacities such as Web Application Firewall (WAF) bypass that frequently requires human intelligence and highly creative way of thinking. Automated web vulnerability scanners will almost inevitably stumble upon this stonewall obstacle and eventually provide a false positive or false negative in the report.

Finally, a vital aspect of automated penetration test to scrutinize is pricing. As detailed above, automated penetration testing cannot be equated to automated vulnerability scanning. Therefore, if someone offers you a price too good to be true it’s probably the case. Intelligent automation may significantly cut human costs, however, on the other side, development of the underlying technology stack is a time-consuming and costly process.


Automated penetration testing brings a great value for small organizations, businesses exempted from strict regulatory requirements, as well as for large enterprises seeking to reasonably reduce their costs while maintaining a decent quality of testing for their applications that are not business critical.

Make sure you carefully select your pentesting company for automated penetration testing, combine it with human-driven penetration testing, and you will likely avoid falling victim to cybercriminals amid skyrocketing threat landscape.

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