Metasploit

1. Mastering Metasploit: A Penetration Testing Foundation

Metasploit isn’t just a tool; it’s an entire framework that provides the infrastructure needed to automate mundane, routine, and complex tasks.

Framework Overview. Metasploit is more than just a collection of exploits; it's a comprehensive framework designed to streamline and automate various aspects of penetration testing. It provides a consistent, reliable library of constantly updated exploits and offers a complete development environment for building new tools and automating every aspect of a penetration test. Understanding its core components—exploits, payloads, encoders, auxiliary modules, and listeners—is crucial for effective use.

Interface Options. Metasploit offers multiple interfaces to suit different user preferences and needs. The most popular is msfconsole, a powerful command-line interface offering flexibility and control. msfcli prioritizes scripting and integration with other command-line tools. Armitage provides a graphical user interface for those who prefer a visual approach.

Commercial Editions. While the core Metasploit Framework is open-source, Rapid7 offers commercial versions like Metasploit Express and Metasploit Pro. These editions provide additional features such as automated password brute-forcing, website attacks, and reporting capabilities, making them suitable for professional penetration testers. However, the fundamental principles and techniques remain the same across all versions.

2. Intelligence Gathering: The Art of Reconnaissance

One of the most important skills a penetration tester can have is the ability to learn about a target, including how it behaves, how it operates, and how it ultimately can be attacked.

Passive and Active Techniques. Intelligence gathering involves collecting information about a target organization to identify potential vulnerabilities and attack vectors. Passive information gathering involves gathering information without directly interacting with the target's systems, using tools like whois lookups and Netcraft. Active information gathering involves direct interaction, such as port scanning with Nmap.

Nmap Integration. Nmap is a powerful port scanning tool that integrates seamlessly with Metasploit. It allows you to scan hosts to identify open ports and running services, which can then be used to identify potential vulnerabilities. Nmap can be run directly from within Metasploit using the db_nmap command, and the results are automatically stored in the Metasploit database.

Advanced Scanning. More advanced techniques, such as TCP idle scanning, allow you to scan a target stealthily by spoofing the IP address of another host on the network. This technique requires identifying an idle host with incremental IP IDs, which can be done using Metasploit's ipidseq auxiliary module.

3. Vulnerability Scanning: Identifying Weaknesses

Vulnerability scanners typically work by fingerprinting a target’s operating system (that is, identifying the version and type) as well as any services that are running.

Automated Assessment. Vulnerability scanners are automated tools used to identify security flaws in systems and applications. They work by fingerprinting the target's operating system and running services, then comparing this information against a database of known vulnerabilities. While vulnerability scanners can be invaluable, they should not be relied upon exclusively, as they can produce false positives and negatives.

Popular Scanners. Several vulnerability scanners can be integrated with Metasploit, including NeXpose and Nessus. NeXpose, offered by Rapid7, provides comprehensive scanning and reporting capabilities. Nessus, from Tenable Security, is another widely used scanner with a large vulnerability database.

Specialized Scanners. In addition to commercial scanners, Metasploit includes several auxiliary modules that can be used to scan for specific vulnerabilities. These include modules for validating SMB logins, scanning for open VNC or X11 servers, and identifying poorly configured Microsoft SQL servers. These specialized scanners can be particularly useful for targeted scanning.

4. Exploitation: The Art of Gaining Access

An exploit should be performed only when you know almost beyond a shadow of a doubt that a particular exploit will be successful.

Exploitation Basics. Exploitation is the process of taking advantage of a vulnerability in a system or application to gain unauthorized access. Metasploit provides a wide range of exploit modules that can be used to target various vulnerabilities. Understanding the basic commands and options within Metasploit is crucial for successful exploitation.

Key Commands. Essential commands include show exploits, show payloads, show options, set, unset, setg, unsetg, and exploit. The search command is useful for finding specific exploits or modules. The info command provides detailed information about a module, including its options and targets.

Exploitation Example. A common exploit is the MS08-067 vulnerability, which affects older versions of Windows. To exploit this vulnerability, you would use the use command to load the exploit module, set the RHOST and PAYLOAD options, and then run the exploit command. Successful exploitation results in a Meterpreter session, providing access to the target system.

5. Meterpreter: The Hacker's Swiss Army Knife

Meterpreter isn’t just a tool; it’s an entire framework that provides the infrastructure needed to automate mundane, routine, and complex tasks.

Post-Exploitation Powerhouse. Meterpreter is an advanced payload within Metasploit that provides a wide range of post-exploitation capabilities. It operates entirely in memory, making it difficult to detect, and offers features such as file system access, process manipulation, privilege escalation, and network pivoting.

Basic Commands. Essential Meterpreter commands include sysinfo (to gather system information), ps (to list running processes), migrate (to move Meterpreter to a different process), hashdump (to extract password hashes), and screenshot (to capture a screenshot of the target's desktop).

Advanced Techniques. Meterpreter also supports advanced techniques such as token impersonation, which allows you to assume the identity of another user on the system. Pivoting allows you to use the compromised system to attack other systems on the internal network. Meterpreter scripts provide additional functionality and automation.

6. Evading Detection: Staying Under the Radar

The information you obtain during a test is vital to the success of the organization’s information security program and in stopping future attacks.

Antivirus Evasion. Antivirus software relies on signatures to detect malicious code. To evade detection, it's necessary to create unique payloads that don't match existing signatures. This can be done using encoders, which modify the code of the payload without changing its functionality.

MSFencode. MSFencode is a tool within Metasploit that helps you to avoid bad characters and evade antivirus and IDSs by encoding the original payload in a way that does not include “bad” characters. Multi-encoding, which involves encoding the payload multiple times, can further increase the chances of evasion.

Custom Templates. Using custom executable templates, rather than the default template, can also help to evade detection. Packers, which compress and encrypt the executable, can also be used to further obfuscate the payload.

7. Client-Side Attacks: Exploiting the Human Factor

Companies invest millions of dollars in security programs to protect critical infrastructures, identify chinks in the armor, and prevent serious data breaches.

Targeting Human Weaknesses. Client-side attacks target vulnerabilities in software commonly used by individuals, such as web browsers, PDF readers, and Microsoft Office applications. These attacks often rely on social engineering techniques to trick users into clicking malicious links or opening infected files.

Browser Exploits. Browser exploits take advantage of vulnerabilities in web browsers to execute code on the target system. These exploits often use heap spraying techniques to increase the likelihood of success. The MS10-002 Aurora exploit, which was used in attacks against Google, is a well-known example.

File Format Exploits. File format exploits involve crafting malicious files that exploit vulnerabilities in applications like Adobe Reader or Microsoft Office. These files are often delivered via email or hosted on malicious websites. The MS11-006 CreateSizedDIBSECTION Stack Buffer Overflow is an example of a file format exploit.

8. Auxiliary Modules: Expanding Your Arsenal

Auxiliary modules in Metasploit can be used for a wide range of purposes.

Beyond Exploits. Auxiliary modules are a diverse set of tools within Metasploit that extend its functionality beyond exploitation. They can be used for reconnaissance, scanning, denial-of-service attacks, fuzzing, and more.

Scanning Modules. Metasploit includes several auxiliary modules for scanning, such as port scanners and service fingerprinters. These modules can be used to identify open ports, running services, and other information about a target system.

Custom Modules. Metasploit's modular design allows you to create your own auxiliary modules to meet specific needs. These modules can leverage the Framework's built-in features, such as TCP, SMB, and auxiliary scanner mixins.

9. Social-Engineer Toolkit: Hacking the Human Mind

Penetration testing is more than running scanners and automated tools and then writing a report.

Exploiting Human Weaknesses. The Social-Engineer Toolkit (SET) is a powerful tool for conducting social engineering attacks. It leverages human psychology to trick individuals into compromising their systems or revealing sensitive information.

Attack Vectors. SET supports various attack vectors, including spear-phishing, website cloning, and infectious media generation. Spear-phishing involves crafting targeted emails with malicious attachments or links. Website cloning involves creating fake websites that mimic legitimate sites to harvest credentials.

Advanced Techniques. SET also includes advanced techniques such as tabnabbing, man-left-in-the-middle attacks, and web jacking. These techniques can be used to further enhance the effectiveness of social engineering attacks.

10. Fast-Track: Automating Penetration Testing

Metasploit isn’t just a tool; it’s an entire framework that provides the infrastructure needed to automate mundane, routine, and complex tasks.

Streamlining Exploitation. Fast-Track is a tool designed to automate and streamline the penetration testing process. It leverages the Metasploit Framework for payload delivery and client-side attack vectors, while adding additional features such as Microsoft SQL attacks and more exploits.

SQL Injection Automation. Fast-Track excels at automating SQL injection attacks. It can automatically detect and exploit SQL injection vulnerabilities in web applications, using techniques such as query string and POST parameter attacks.

MSSQL Bruter. The MSSQL Bruter is a powerful tool for brute-forcing Microsoft SQL Server credentials. It can use various authentication methods and wordlists to identify weak or default passwords, providing a quick way to gain access to the database server.

11. Karmetasploit: Wireless Network Exploitation

Penetration testing is about ignoring an organization’s perception of its security and probing its systems for weaknesses.

Exploiting Wireless Clients. Karmetasploit is a Metasploit implementation of the KARMA attack, which targets wireless clients by exploiting their tendency to automatically connect to known networks.

Fake Access Points. Karmetasploit sets up a fake access point that mimics the ESSIDs of networks the target client has previously connected to. When the client connects to the fake access point, Karmetasploit can intercept their traffic and launch various attacks.

Evil Services. Karmetasploit implements various "evil" services, such as DNS, POP3, IMAP4, SMTP, FTP, and SMB, which can be used to capture credentials and deliver malicious payloads.

12. Custom Modules: Tailoring Metasploit to Your Needs

As you grow more comfortable with Metasploit, you will notice that the Framework is frequently updated with new features, exploits, and attacks.

Extending Metasploit. Metasploit's modular design allows you to create your own modules to meet specific needs. This involves writing Ruby code that leverages the Framework's built-in features and APIs.

Module Structure. A typical Metasploit module includes a super block that defines the module's name, description, author, license, and other metadata. It also includes an exploit section that defines the steps involved in exploiting the vulnerability.

PowerShell Example. A custom module can be created to deliver payloads via Microsoft SQL using PowerShell. This involves converting the payload to hexadecimal, transmitting it to the target system, and then using PowerShell to convert it back to an executable.

Last updated: April 14, 2025