Penetration Testing And Vulnerability Scanning

In this article, I will explore the domains of vulnerability scanning and penetration testing, highlighting the subtle differences and similarities between the various stages and processes involved in each step. I will also take a closer look at a few tools at the end which focus on the automation of the task. To make things simple and educational, I will break down the fundamental steps of a pentest and vulnerability assessment. Let's get started!

Table of content

• What is Penetration testing?
  • Planning and Recon
  • Scanning
  • Exploitation and Gaining Access
  • Maintaining Access
  • Report and Control
• What is Vulnerability Scanning?
• Penetration testing tools.
• Automation of Penetration testing.
• Pentesting Automation Workflow development
• Automation with Open-Source Solutions

What is Penetration testing?

Penetration testing, also known as pentesting, is a process that involves identifying and resolving security vulnerabilities by simulating a friendly hacker. It is a systematic approach that begins with planning and collecting information and, depending on the objective, concludes with reporting the findings or ensuring continuous access. This is a standard procedure that aids in enhancing the security of an organization's digital environment. The following are the stages involved:

Planning and Recon

During the planning phase, it is crucial to obtain all relevant information about the target, including details about the technology they use and their data in case of a phishing attack. This information plays a vital role in determining the tools, techniques, and other details that will shape the entire process.

The next step is a survey, which involves collecting most of the essential data. There are two basic approaches to reconnaissance: active and passive. While both methods achieve the same goal, active reconnaissance is more assertive and likely to be noticed. In contrast, passive reconnaissance gathers information indirectly and is more covert and difficult to identify. Each method has a different operating time, with passive methods sometimes being more complex and time-consuming, while active methods are quicker but less detailed.

Scanning

The process of scanning is similar to conducting an exhaustive investigation. The main objective is to dig deeper into the target and gather valuable information. It is similar to sifting through a messy pile of things to find the hidden gems.

Our goal is to obtain crucial information that will enable us to break into the system with minimum suspicion. We utilize various scans that are tailored to the task at hand. For instance, when working with a web application, we search for vulnerabilities such as CSRF potential and XSS endpoints. We examine access points, investigate services running on ports, and determine the presence of firewalls or WAFs on a network. The options available for scanning are numerous and varied.

Exploitation and Gaining Access

Once a hacker discovers a vulnerability that can be exploited, it can take only a short time to launch a full-scale attack. Exploiting a vulnerability involves gaining unauthorized access to a victim's system. Attackers need to be cautious and avoid direct contact with the target system to avoid getting caught.

There are multiple scenarios for illegal access, but the most common ones are Remote Code Executions (RCEs) and backdoors. RCE vulnerabilities are core-based issues that allow for unwanted input or output and sometimes manipulation of the code logic. RCEs are the most dangerous type of vulnerability and often have a large bounty on them. Backdoors come in two types - custom and misconfig. Custom backdoors involve tricking the target into downloading a malicious file, while misconfig backdoors involve accessing a developer portal.

Maintaining Access

Let's discuss the concept of preserving access in more detail. Consider having a backup key stored in a secure location in case your primary key gets lost, or you need to take an unexpected break. This backup access not only serves as a precautionary measure but also enables you to navigate the digital world effortlessly. Having access to essential information at all times is another benefit. Therefore, keeping access is like having a reliable companion with you on your digital journey, ensuring that you are always prepared for any situation that may arise.

In the case of the victim's machine, the backup access is like a stolen backup key. The hacker can easily access the victim's personal or professional space whenever they want, without being detected if they play it safe.

Report and control

As an ethical hacker, creating a report is crucial to your job. In the report, you must explain every step you have taken, the issues you have discovered, the exploits you have used, the assets that are at risk, and the results you have obtained. Although the report can be a daunting task, the information it contains is valuable. Knowing which assets are at risk can help the company prioritize attack prevention to secure the infrastructure effectively.

However, the process of penetration testing is not as complicated as it may seem at first. It primarily involves understanding the implications of the testing. Hackers generally have a good understanding of this concept, but some specialize in specific tasks within the process.

What is Vulnerability Scanning?

We will now discuss vulnerability scanning, a segment of the pen-testing process. This phase falls under the scanning phase and involves going through a large list of issues and misconfigurations. The vulnerability assessment process aims to analyze a lot of data and research reverse engineering exploits and bugs that cause the vulnerabilities. Online databases such as exploit-db have listings of exploits for CVEs that are often referred to. These databases provide information such as exploit-related PoC code and other relevant details.

Vulnerability assessment requires a lot of time and effort to be invested. The objective here is to find an exploit, and the more accurate the exploitation, the better the understanding of the information. For example, if you have a task regarding CSP analysis, you may discover that the CSP Policy is in place to protect the web application from possible XSS attacks. However, even if the wildcard is present, you won't be able to exploit it without knowing the vulnerable endpoints. If there are no possible or accessible endpoints for XSS on the website, how will you exploit it? In such scenarios, a deeper understanding of the situation is necessary.

Thus, vulnerability scanning and assessment is a crucial yet time-consuming task that requires a thorough understanding of the interrelationship between different pieces of information.

Penetration testing tools

Over time, penetration testing tools have undergone a significant evolution that has mirrored the constantly shifting landscape of cybersecurity threats. Early tools were frequently simple and had a narrow range of uses. However, penetration testing tools have developed into strong, comprehensive solutions in response to the growing sophistication of cyber threats. These tools give organizations a thorough understanding of their security posture by simulating actual cyberattacks in addition to identifying vulnerabilities.

Notable advancements have been made in vulnerability assessment tools. Cutting-edge technologies like artificial intelligence and machine learning are used by modern tools to improve their capacity to recognize and rank vulnerabilities. To keep these tools up to date with the most recent cyber threats and vulnerabilities, the integration of threat intelligence feeds has become a standard feature. Furthermore, intuitive user interfaces have increased the accessibility of these tools for a wider range of security professionals.

Exploitation frameworks, exemplified by widely used platforms like Metasploit, have also undergone significant development. These frameworks now offer a more user-friendly experience, enabling security experts to automate the exploitation process efficiently. The frameworks have evolved to support a broader range of vulnerabilities and have become essential components of penetration testers' arsenals. Integration with threat intelligence sources has further enhanced the precision and effectiveness of exploitation attempts.

Automation of Penetration testing.

The automation of penetration testing processes has transformed the efficacy and efficiency of security assessments. Automation speeds up testing, allowing businesses to conduct more frequent and in-depth security assessments. Platforms for orchestration have become essential elements, offering a centralized framework for managing the whole penetration testing lifecycle. With the help of these platforms, security teams can streamline resource usage and shorten assessment times by automating repetitive tasks like vulnerability scanning and exploit execution.

One notable development in automation is how well it integrates with DevOps processes. Penetration testing tools are evolving to fit cleanly into DevOps workflows as more companies embrace them for continuous and faster software delivery. Security is a crucial component of the software development lifecycle because automation guarantees the incorporation of security testing at different phases of the development pipeline.

Automation also applies to cloud environments, where instruments are created or modified to evaluate the security of cloud infrastructure. With the popularity of serverless computing, new challenges have emerged. To provide thorough security assessments for serverless architectures, automated tools are tackling these challenges.

In summary, the development of penetration testing tools and the incorporation of automation into workflows represent a dynamic reaction to the changing nature of the threat landscape. With

increasingly advanced and effective tools available, security professionals can now outmanoeuvre cyber adversaries and improve an organization's overall security posture. The constant endeavour to safeguard sensitive data and digital assets will depend heavily on these tools' continued advancements as technology moves forward

Pentesting Automation Workflow development

There are several issues to consider when creating a workflow-based automation system for penetration testing. Clearly defining goals and evaluating current procedures are the first steps in identifying areas that are ready for automation. Selecting the right tools is essential, requiring a balance between adaptability, integration potential, and customization choices.

A crucial step in the process is designing the workflow sequence, which necessitates a logical flow of tasks from reconnaissance to reporting. The development pipeline and security testing are guaranteed to work together seamlessly when DevOps practices are integrated. Moreover, taking into account cloud and hybrid environments necessitates adjustment to the particular difficulties these settings present.

Regular testing and ongoing monitoring are essential elements that call for proactive measures to quickly identify and neutralize new threats. For the security team to understand and use the system effectively, comprehensive documentation of the automated workflow and training is necessary.

Imagine a situation where a security expert is assigned to test a web application for vulnerabilities. Finding potential weaknesses in the web infrastructure of the application is the goal. This example concentrates on web application enumeration, the first step in the penetration testing process.

The next step is to use Nmap to scan the network for open ports and web server services. Understanding the attack surface and potential entry points requires knowledge of this information. Nmap uses the output from Sublist3r to direct a targeted scan that is concentrated on the subdomains that are found. After the network scan, attention turns to scanning web applications. Tools like Burp Suite are used to find common vulnerabilities like SQL injection and cross-site scripting. Burp Suite's configuration is based on the findings of the network scan, which guarantees a targeted and effective evaluation.

The process includes directory and file enumeration using Dirb to hone the analysis further. Using the web application scan data as a guide, this step looks for hidden resources on the web server. The settings of Nikto, a program for more thorough vulnerability analysis, are influenced by the findings from Dirb. Nikto provides a comprehensive report on possible security risks by scanning the web server for known vulnerabilities, misconfigurations, and out-of-date software versions.

These tools' smooth workflow integration demonstrates how interconnected they are. Web application enumeration is made easier by a streamlined process where the output of one tool influences the configuration of another. To interpret results, modify configurations, and spot possible exploitation points, a security professional's experience is crucial to the workflow's success. The workflow must be continuously improved to keep up with changing threats and preserve the web application's security posture over time. Creating and managing these workflows requires constant attention to detail and knowledge of the rapidly changing cybersecurity landscape.

But it's critical to recognize how complicated and challenging this process is. The complexity of creating and managing a strong automation workflow increases as businesses try to stay ahead of the constantly changing landscape of cyber threats. The inherent challenges of penetration testing automation are attributed to the dynamic nature of IT environments, the diversity of testing requirements, and the constantly evolving threat landscape. It takes constant commitment, skill development, and a sophisticated grasp of the unique security requirements of the company to navigate this complexity. Creating an automated penetration testing workflow that works well and is flexible is a difficult task that needs ongoing attention to detail and experience to stay ahead of the cybersecurity curve.

Automation with Open-Source Solutions

The development of workflows with tools that easily integrate into them is crucial in the constantly changing field of cybersecurity. There are multiple solutions one can come up with to develop a fully automated code that works for all possibilities, and the other easier way is to use a ready-made solution. I will explain both solutions.

Code the system

We will discuss the steps on how we can code this cause I just know the process, not the entire thing. It’s mainly dependent on what you want to automate. There are multiple things you can automate in cybersecurity mainly in pen-testing. If you are building from scratch it’s not feasible to build an entire system from scratch all alone by yourself, If you want to do that get a group of programmers and other people and start a company for that. The best course of action here is to build multiple scripts that work on the same principle but do different tasks.

In the programming of such automation, we need to consider a few things:

• The complexity: The number of tools used and steps one tool takes to complete the task. For instance, let’s say I am scanning a website, and I use 3 tools for this job: Amass, Nmap, and DnsDumpster. All three can be used for web app enumeration. We will see how these are connected in a bit.
• The Time: The Time taken by this integration is a lot. Developing anything from scratch takes time to develop and revise. In this case, the time taken boils down to research. Mainly how the different components or tools can be integrated, let’s say I want to integrate Nmap with Nikto and Wpscan. What am I looking for in Nmap that can better help in optimization and as an upgrade?
• The Coding: There are a few things to consider while coding this and they are mainly output handling the output raw data. Based on your research and requirements, you can use regex to extract the necessary data like the URL, IP, Port, etc. This is important as this is how you are going to connect this entire map.

So, based on that, let’s assume I am going to collect subdomain addresses, extract the IP addresses, and then do a script-based vuln analysis using Nmap. And this is how it looks:

So, in the above image, I have shown how we can interconnect three tools. I know it’s kind of pointless to use DnsDumpster in the middle, but it’s just a reference. This is how we can integrate it. At least one of the ways we can do this is to add more tools and all other sophistication and optimizations to this and make it more complex, but let’s keep it simple.

Imagine now the potential that arises from creating your security processes from scratch with an emphasis on automation and efficiency. You need some basic tools before you can set out on such a journey. Python is a powerful ally for scripting and automation, with many packages that fit in well with the workflow development process. Sublist3r is quite useful for enumerating every subdomain. Take advantage of Nmap's capabilities for network scanning. Use Burp Suite to improve web application scanning, Dirb to enumerate directories and files, and Nikto to conduct in-depth vulnerability analysis. Combined, these tools provide a strong and efficient workflow for penetration testing.

But the adventure doesn't end with just tools. Explore Python packages for Continuous Integration and Continuous Deployment (CI/CD) on GitHub to incorporate collaborative elements. Using tools like GitHub Actions, GitLab CI, or Jenkins to set up a continuous integration and testing pipeline guarantees that your workflow is effective and updated and tested regularly. Your security automation solution gains additional sophistication from this integration with CI/CD processes, guaranteeing its flexibility in the face of changing cybersecurity threats.

Use an existing system.

So for the ones who are not able to code the system or are too lazy to do so and want an easy solution, I have your back I have a list of tools that can automate the task for you. The tools listed below are like this: the open-source tools focus on certain aspects of the process and not the entire process. Now, let’s get down to the tools listing. The links for the open-source tools are mentioned in the sources:

• Rayder: This is a tool that is a workflow application simplified to run complicated Orchestration mapping. This tool uses YAML to map different commands and tools to run recon tasks. This tool allows us to mention how the commands must execute save and locate the outputs.
• MetaHub: MetaHub is a contextualizing framework that helps automate the compilation and contextualization of all the assets based on the environments and the core requirements. This tool is for cloud and AWS-related operations, not focusing on any of the regular tasks.
• Vortex: This tool is automation for multiple tasks, including recon, enumeration, and finally, exploitation. It’s a crazy good tool and a must-try.
• Osmedeus: This is a huge framework, and it covers almost all requirements to make a good enumeration and recon framework for automation. This tool scans git repos, domains, and cloud distributions. So yes, this is huge, fast, and reliable.

These were the four free options I could find worth sharing with you all. I will share the links to each of them below. You can check them out if you are interested. If you also want to try a few more automation tools that I came up with, you can check my GitHub repos, and if you like them, then give them a star or join the discussions to give your views and ideas.

This was my take on the automation of pen-testing, either by programming it or by using existing solutions. The final aim of ours is to hack the systems in one or the other way.

Source

• Rayder
• MetaHub
• Vortex
• Osmedeus
• Synopsys
• Cloudflare