23 May, 2023

Intelligent Reconnaissance: How AI Tools Drive Effective Penetration Testing

Penetration Testing as a service (PTaaS)

Tests security measures and simulates attacks to identify weaknesses.

With the ever-increasing complexity of cybersecurity threats, organizations are continually seeking innovative approaches to safeguard their computer systems. Penetration testing, a fundamental practice in the realm of cybersecurity, plays a pivotal role in identifying vulnerabilities and fortifying defenses against potential attacks. In this blog, we will explore the remarkable potential of AI-powered tools and their profound impact on the reconnaissance phase of penetration testing. By leveraging the capabilities of artificial intelligence, organizations can streamline and enhance their reconnaissance efforts, leading to more efficient and effective security measures. Join us as we dive into the world of AI and discover how it is reshaping the landscape of penetration testing, backed by compelling data that highlights its transformative influence. 

Significance of Reconnaissance in Penetration Testing 

Reconnaissance, often referred to as the “information gathering” phase, is a critical component of the overall penetration testing process. It involves collecting comprehensive information about the target system, network, or organization under assessment. The primary objective of reconnaissance is to gain insights into the target’s infrastructure, identify potential vulnerabilities, and understand the landscape that attackers may exploit. 

Identifying Vulnerabilities: Reconnaissance serves as the initial step in identifying potential vulnerabilities in the target system. By gathering information about the system’s architecture, software versions, network topology, and other relevant details, security professionals can gain a comprehensive understanding of the potential weak points that could be exploited by attackers. 

Understanding Attack Surfaces: During reconnaissance, the penetration tester seeks to discover all available attack surfaces and potential entry points into the target system. This includes analyzing network configurations, identifying publicly accessible services, and exploring potential entry vectors such as web applications, email systems, or wireless networks. By comprehensively mapping the attack surface, testers can prioritize their efforts and focus on the most critical areas. 

Leveraging Open-Source Intelligence (OSINT): Reconnaissance involves gathering information from publicly available sources, known as Open-Source Intelligence (OSINT). This includes analyzing websites, social media profiles, public databases, job postings, and other sources to collect valuable information that can aid in identifying potential vulnerabilities or social engineering opportunities. OSINT plays a crucial role in understanding the target’s digital footprint and potential points of weakness. 

Assessing Security Posture: Reconnaissance provides insights into the target organization’s security posture. It helps in understanding their security measures, configurations, and policies in place, allowing penetration testers to evaluate the effectiveness of existing defenses. By examining network diagrams, security documentation, and other relevant resources, testers can assess the strength of the target’s security infrastructure and identify areas that require improvement. 

Tailoring Attack Strategies: Effective reconnaissance enables penetration testers to tailor their attack strategies specifically to the target system or organization. The information gathered during this phase helps testers choose the appropriate tools, techniques, and methodologies to exploit identified vulnerabilities. This customized approach increases the chances of uncovering critical security flaws and emulates the real-world tactics employed by malicious actors. 

Risk Assessment and Prioritization: Reconnaissance assists in conducting a comprehensive risk assessment by identifying potential attack vectors and vulnerabilities. This information allows security professionals to prioritize their efforts and allocate resources efficiently. By understanding the severity and potential impact of each vulnerability, organizations can focus on remediation activities that address the most critical risks first. 

Compliance and Regulatory Requirements: Reconnaissance also plays a crucial role in meeting compliance and regulatory requirements. By thoroughly understanding the target environment and documenting vulnerabilities and security gaps, organizations can demonstrate their commitment to security and comply with relevant industry standards and regulations. 

How ChatGPT and AI Tools Transform Reconnaissance  

The scope of ChatGPTs and AI tools in helping reconnaissance of pen testing is vast and continually expanding. These advanced technologies have the potential to streamline and enhance the reconnaissance phase, providing security professionals with valuable insights and automating certain tasks. Here are some key areas where ChatGPTs and AI tools can contribute to reconnaissance in pen testing: 

Automated Information Gathering: ChatGPTs and AI tools can automate the process of gathering information from various sources. They can scrape websites, social media platforms, forums, and other online repositories to extract relevant data. By automating this process, AI tools significantly reduce the time and effort required to collect information, enabling penetration testers to focus on analysis and decision-making. 

Natural Language Processing (NLP): NLP algorithms enable AI tools to process and analyze large volumes of text-based data efficiently. These algorithms can extract keywords, identify patterns, and recognize relationships within the gathered information. NLP-powered tools can help uncover hidden information, understand context, and extract actionable intelligence from textual data sources. 

Image and Video Analysis: AI algorithms excel at image and video analysis, allowing for the identification and extraction of valuable information from visual content. For example, AI-powered tools can analyze screenshots or security camera footage to detect logos, sensitive information, or potential vulnerabilities. Such capabilities aid in reconnaissance by providing visual insights that may not be readily apparent through manual examination. 

Network Mapping and Fingerprinting: AI-based network scanning tools can automatically map and fingerprint network infrastructure. These tools can identify active hosts, network devices, open ports, and services running on the target system. By leveraging AI algorithms, reconnaissance can be conducted swiftly and accurately, resulting in a comprehensive understanding of the target’s network architecture. 

Threat Intelligence Analysis: AI tools can process and analyze vast amounts of threat intelligence data. By leveraging machine learning algorithms, these tools can identify emerging threats, patterns, and indicators of compromise. Integrating threat intelligence analysis into the reconnaissance phase provides penetration testers with valuable information about potential risks and attack vectors, enhancing the effectiveness of the overall testing process. 

Pattern Recognition and Anomaly Detection: AI tools can be trained to recognize patterns and identify anomalies within collected data. This capability aids in identifying suspicious or potentially malicious activities during the reconnaissance phase. AI algorithms can analyze network traffic, logs, or system behavior to detect unusual patterns or deviations from expected norms, assisting in the identification of potential vulnerabilities or indicators of compromise. 

Integration with ChatGPTs for Interactive Reconnaissance: ChatGPTs can be utilized as interactive interfaces, allowing penetration testers to engage in natural language conversations with AI systems. This enables security professionals to ask targeted questions, seek clarification, and receive real-time insights and recommendations during the reconnaissance process. ChatGPTs enhance the efficiency and effectiveness of reconnaissance by providing on-demand information and guidance. 

It’s important to note that while AI tools and ChatGPTs offer tremendous potential in reconnaissance, they are not meant to replace human expertise and judgment. They should be utilized as powerful assistants to augment and streamline the reconnaissance process, enabling security professionals to focus on critical analysis, decision-making, and the interpretation of results. 

Handson with ChatGPT  

ChatGPT can be effectively utilized to automate reconnaissance tasks, such as requesting a vital list of server paths that can be tested for path traversal vulnerabilities. Additionally, it can be prompted to extract beneficial information from source code by creating non-intrusive and clever prompts, allowing ChatGPT to dig into the details and retrieve relevant data. This automation of reconnaissance tasks through ChatGPT streamlines the process and enhances efficiency. 

Path Enumeration with ChatGPT leads to sensitive data exposure on the site 

To identify available paths on a website, we require a list of site-specific paths that can be manually tested or checked using tools like Burp Suite. In this case, we are conducting tests on a vulnerable website meant for practice, specifically https://hack-yourself-first.com/. It’s important to mention that ChatGPT does not respond to intrusive prompts. Therefore, to obtain the desired results, we aim to deceive ChatGPT by presenting text that appears educational in nature, ensuring we receive the desired information. 

Approach 1: Create a prompt that instructs ChatGPT to generate an educational list of significant server paths. 

Ask again to create more holistic coverage of paths. 

Approach 2: Now, we will examine the generated path to verify its importance in producing desired outcomes. To do this, we will access the website and sequentially add the created paths. This can be a tedious task, especially when dealing with a large list of paths. To simplify the process, we can use Burp Intruder to automatically test all the paths. In this specific scenario, we will focus on the Robots.txt path (/robots.txt). 

Note: The robots.txt file is a text file that is placed in the root directory of a website to provide instructions to web robots or crawlers, also known as web spiders or bots. These bots are used by search engines and other web services to scan and index web pages. 

The robots.txt file contains directives that specify which parts of a website the bots are allowed to access and crawl, and which parts should be excluded. It helps control the behavior of search engine crawlers and prevents them from accessing certain pages or directories that the website owner wants to keep private or hidden from search results. 

The format of a robots.txt file consists of user-agent directives and disallow directives. User-agent directives specify the specific bots to which the following directives apply. The “*” symbol is a wildcard character that represents all bots. Disallow directives specify the URLs or directories that are not to be accessed by the specified bots. 

For example, a robots.txt file that disallows all bots from accessing the “/private” directory would contain the following directive: 

User-agent: * Disallow: /private/ 

Observe that appending /robots.txt gives more insight about possible paths, let’s append ‘/api/admin/users’ to test more functionality. It is to be noted that the site has revealed list of all users and there credentials without any authentication and ChatGpt helped to unrevealed IDOR vulnerability on the site. 

Testing for Click Jacking with ChatGPT 

Clickjacking, also known as UI redress attack, is a malicious technique used by attackers to deceive users into clicking on hidden or disguised elements on a website, without their knowledge or consent. The attacker overlays or embeds legitimate website content with malicious elements, making users unknowingly perform actions they didn’t intend, such as clicking on buttons or links that trigger unauthorized actions. Clickjacking poses a significant threat to user privacy and security. However, ChatGPT can be utilized to address clickjacking concerns. It can help in educating users about the risks associated with clickjacking and provide guidance on preventive measures. By offering clear and concise explanations, ChatGPT can empower users to recognize clickjacking attempts and take appropriate actions to safeguard their online interactions. Additionally, ChatGPT can assist website developers and security professionals in understanding and implementing countermeasures, such as implementing frame-busting scripts or utilizing X-Frame-Options headers, to mitigate clickjacking vulnerabilities. 

Approach 1: In this scenario, we can utilize ChatGPT to generate a template for testing clickjacking on the target host and gather information regarding the website’s susceptibility to this type of attack. 

Approach 2: To determine whether a website is susceptible to clickjacking, you can create an HTML file and view it in a web browser for verification. 

Notice that the code provided by ChatGPT assisted us in conducting the vulnerability assessment. 

Enumerate Subdomain with ChatGPT 

Let’s Create a prompt on ChatGPT to create a code in python which will enumerate subdomains of the host. 

Approach 1: Copy this generated code and create a Python file in any Python-supported IDE. Run the code and validate if the subdomain enumeration is successful on the device or not. 

In this case, we need to add a comprehensive list for subdomain enumeration to improve the process. Additionally, we can create a prompt to allow the user to input a high-quality list of subdomains for more accurate and effective results. 

As information gathering and reconnaissance play a vital role in planning subsequent exploits, the techniques employed in reconnaissance always require new suggestions to gather the desired amount of information. By utilizing an interactive prompt with ChatGPT, we have the flexibility to design and generate as much information as we need. The extent of information obtained largely depends on the type of prompt we create. 

Automated AI Tools for Reconnaissance 

Now that we have utilized ChatGPT for reconnaissance, let’s explore some open-source tools that harness the power of ChatGPT to automate the reconnaissance tasks. 

In this article, we will explore a particular open-source proof-of-concept (PoC) called “GPT_Vuln-analyzer” that has not yet been developed into a full-fledged tool. 

The GPT_Vuln-analyzer is a Proof of Concept (PoC) application that showcases the potential of using Artificial Intelligence (AI) for vulnerability analysis. The tool combines several modules and technologies, including the openai-api, python-nmap, dnsresolver, customtkinter, and tkinter. 

The primary purpose of GPT_Vuln-analyzer is to leverage AI capabilities, specifically the ChatGPT model from OpenAI, to generate accurate results for vulnerability analysis. By integrating AI into the process, the tool aims to enhance the efficiency and effectiveness of vulnerability assessment. 

The application offers both a Command Line Interface (CLI) and a Graphical User Interface (GUI) version, providing flexibility and ease of use for different users. The CLI allows for executing commands and performing tasks directly from the command line, while the GUI provides a visual interface for interacting with the tool. 

GPT_Vuln-analyzer encompasses various functionalities related to network security. It includes network vulnerability analysis, utilizing the python-nmap module, which enables scanning and identifying vulnerabilities within network systems. Additionally, the tool incorporates DNS enumeration, which involves gathering information about DNS records and configurations, and subdomain enumeration, which involves discovering subdomains associated with a target domain. 

The integration of AI technology with these functionalities enables the tool to provide more accurate and insightful vulnerability analysis results. By leveraging the capabilities of the ChatGPT model, the application can process and interpret complex information related to vulnerabilities, enhancing the quality of analysis and assessment. 

Overall, the GPT_Vuln-analyzer demonstrates the potential of AI in vulnerability analysis, combining it with modules for network vulnerability analysis, DNS enumeration, and subdomain enumeration. It offers both a CLI and GUI interface, allowing users to interact with the tool conveniently. The aim is to improve the accuracy and efficiency of vulnerability analysis by harnessing the power of AI. 

How to use this tool? 

Step 1: Clone this tool from https://github.com/morpheuslord/GPT_Vuln-analyzer.git  

Command: $ git clone https://github.com/morpheuslord/GPT_Vuln-analyzer.git 

Step 2: Import any packages you want to test this POC as shown in step 3. 

Command: cd package && pip3/pip install . 

Step 3: This is the packages offered in this PoC to test, import the packages as shown below. 

Step 4: Change the the “API__KEY” part of the code with OpenAI api key and the IPGeolocation API key 


 gkey = “__API__KEY__” # Enter your IPGeolocation API key 
akey = “__API__KEY__” # Enter your OpenAI API key 

Step 5: Install the packages 


pip3 install -r requirements.txt 


pip install -r requirements.txt 

Step 6: run the code python3 gpt_vuln.py with reference shown below. 

Step 7: Observe the result 


In conclusion, while there is currently no stable solution specifically focused on AI-powered vulnerability analysis, we can leverage the capabilities of OpenAI and integrate it with other open-source tools for penetration testing. The GPT_Vuln-analyzer Proof of Concept application demonstrates the potential of using AI in vulnerability analysis, but further development is needed for a comprehensive and stable AI tool dedicated to this purpose. However, by combining OpenAI with existing open-source tools, we can enhance the effectiveness of penetration testing and leverage AI technology to improve the accuracy and efficiency of vulnerability assessment. Continued research and development in this field hold promise for the future of AI-powered solutions in vulnerability analysis and penetration testing. 

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