SEC580: Metasploit for Enterprise Penetration Testing

  • Online
12 CPEs

SEC580 will teach you how to apply the incredible capabilities of the Metasploit Framework in a comprehensive penetration testing and vulnerability assessment regimen. In this course, you will learn how Metasploit can fit into your day-to-day penetration testing assessment activities. You'll gain an in-depth understanding of the Metasploit Framework far beyond how to exploit a remote system. You'll also explore exploitation, post-exploitation reconnaissance, token manipulation, spear-phishing attacks, and the rich feature set of the Meterpreter, a customized shell environment specially created for exploiting and analyzing security flaws.

What You Will Learn

Many enterprises today face regulatory or compliance requirements that mandate regular penetration testing and vulnerability assessments. Commercial tools and services for performing such tests can be expensive. While really solidsolid free tools such as Metasploit are available, many testers do not understand the comprehensive feature sets of these tools and nor how to apply them in a professional-grade testing methodology. Metasploit was designed to help testers confirm vulnerabilities using an open-source and easy-to-use framework. This course will help students get the most out of this free tool.

SEC580 will show students how to apply the incredible capabilities of the Metasploit Framework in a comprehensive penetration testing and vulnerability assessment regimen, and according to a thorough methodology for performing effective tests. Students who complete the course will have a firm understanding of how Metasploit can fit into their penetration testing and day-to-day assessment activities. The course will provide an in-depth understanding of the Metasploit Framework far beyond simply showing attendees how to exploit a remote system. The class will cover exploitation, post-exploitation reconnaissance, anti-virus evasion, spear-phishing attacks, and the rich feature set of the Meterpreter, a customized shell environment specially created to exploit and analyze security flaws.

The course will also cover many of the pitfalls that a tester may encounter when using the Metasploit Framework and how to avoid or work around them, making tests more efficient and safer.

Syllabus (12 CPEs)

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  • Overview

    Section 1 is designed to help attendees master the most heavily used exploitation framework on the planet and see how they can wield it effectively in professional penetration testing. We analyze some of the most powerful and yet often overlooked capabilities of the Metasploit Framework, using numerous exercises that make this one of the most hands-on courses ever developed by SANS.

    You will go from zero to exploit and beyond faster than you ever thought possible. For example, after this course section you will understand the Ruby foundations of Metasploit and how interacting with these underpinnings will greatly optimize and enhance your testing activities. Further, you will understand how far you can extend your exploitation activities through the effective use of some of the late-breaking features of the amazing Meterpreter. Finally, have you ever wondered how you can compromise an entire domain from simple Windows system access? After this section you will know exactly how to achieve this kind of result. After all, shell is only the beginning.

    • Guided Overview of Metasploit's Architecture and Components
    • Deep Dive into the Msfconsole Interface, including Logging and Session Manipulation
    • Careful and Effective Exploitation
    • The Ultimate Payload: The Metasploit Meterpreter In-Depth
    • Metasploit's Integration into a Professional Testing Methodology
    • Automation with Meterpreter Scripts to Achieve More in Less Time with Consistency
    • It's Not All Exploits - Using Metasploit as a Recon Tool
    • Using Auxiliary Modules to Enhance your Testing
    • Ultra-Stealthy Techniques for Bypassing Anti-Virus Tools
    • Client-Side Attacks - Using One-Liners instead of Executables
    • Port and Vulnerability Scanning with Metasploit, Including Integration with Nmap, Nessus, and Qualys
    • Capturing SMB Credentials and Metasploit's awesome PowerShell integration
  • Overview

    In this second section we build upon the deep foundations of section 1 to see how Metasploit can be used within a penetration tester's ecosystem of tools and techniques to attack systems in new and creative ways. We'll analyze the activities of the most effective bad guys to see how they target enterprises via complex and often non-traditional attack vectors so that we can model their behaviors in our penetration testing processes. Client-side attacks launched via email, phishing, and document payload attacks are currently some of the most heavily used attack vectors. The bad guys use these techniques because they almost always work. The course shows penetration testers how to wield such attacks to determine the business implications of vulnerabilities, all with the objective of improving the target organization's security stance.

    • Merciless Pivoting: Routing Through Exploited Systems
    • Exposing Metasploit's Routing Using SOCKS Proxies
    • Privilege Escalation Attacks
    • Metasploit's Integration with Other Tools
    • Making the Most of Windows Payloads
    • Advanced Pillaging - Gathering Useful Data from Compromised Machines
    • Evading Countermeasures to Mimic Sophisticated Attackers
    • Scripting Up the Meterpreter to Customize Your Own Attacks
    • Persisting Inside an Environment
    • Carefully Examining Your Attack's Forensic Artifacts
    • Integration with CrackMapExec, a Stand-alone Testing Tool
    • Command and Control via Third-Party Infrastructure

Laptop Requirements


A properly configured system is required to fully participate in this course. If you do not carefully read and follow these instructions, you will likely leave the class unsatisfied because you will not be able to participate in hands-on exercises that are essential to this course. Therefore, we strongly urge you to arrive with a system meeting all the requirements specified for the course.

Host Operating System: Latest version of Windows 10/11, macOS 10.15.x or later, or Linux that also can install and run VMware virtualization products described below. Those who use a Linux host must also be able to access exFAT partitions using the appropriate kernel or FUSE modules. Note: Apple systems using the M1 processor cannot perform the necessary virtualization at this time and cannot be used for this course.

You also must have 8 GB of RAM or higher for the two virtual machines to function properly in the class.

It is critical that your CPU and operating system support 64-bit instructions so that our 64-bit guest virtual machines will run on your laptop.

In addition to having 64-bit capable hardware, AMD-V, Intel VT-x, or the equivalent must be enabled in BIOS/UEFI.

Download and install either VMware Workstation Pro 15.5.x, VMware Player 15.5.x or Fusion 11.5.x or higher versions before class. If you do not own a licensed copy of VMware Workstation or Fusion, you can download a free 30-day trial copy from VMware. VMware will send you a time-limited serial number if you register for the trial at their website.

Other virtualization software, such as VirtualBox and Hyper-V, are not appropriate because of compatibility and troubleshooting problems you might encounter during class.

VMware Workstation Pro and VMware Workstation Player on Windows 10 is not compatible with Windows 10 Credential Guard and Device Guard technologies. Please disable these capabilities for the duration of the class, if they're enabled on your system, by following instructions in this document.


  • CPU: 64-bit 2.0+ GHz processor or higher-based system is mandatory for this class (Important - Please Read: a 64-bit system processor is mandatory)
  • BIOS/UEFI: VT-x, AMD-V, or the equivalent must be enabled in the BIOS/UEFI
  • RAM: 8 GB (gigabytes) of RAM or higher is mandatory for this class (Important - Please Read: 8 GB of RAM or higher is mandatory)
  • Wireless Ethernet 802.11 B/G/N/AC
  • Disk: 60 Gigabytes of free disk space
  • Latest version of Windows 10/11, macOS 10.15.x or later, or Linux
  • VMware Workstation Pro 15.5.X+, VMware Player 15.5.X+ or Fusion 11.5+

Your course media will now be delivered via download. The media files for class can be large, some in the 40 - 50 GB range. You need to allow plenty of time for the download to complete. Internet connections and speed vary greatly and are dependent on many different factors. Therefore, it is not possible to give an estimate of the length of time it will take to download your materials. Please start your course media downloads as you get the link. You will need your course media immediately on the first day of class. Waiting until the night before the class starts to begin your download has a high probability of failure.

SANS has begun providing printed materials in PDF form. Additionally, certain classes are using an electronic workbook in addition to the PDFs. The number of classes using eWorkbooks will grow quickly. In this new environment, we have found that a second monitor and/or a tablet device can be useful forby keeping the class materials visible while the instructor is presenting or while you are working on lab exercises.

Author Statement

Metasploit is the most popular free exploitation tool available today. It is in widespread use by penetration testers, vulnerability assessment personnel, auditors, and real-world threat actors. However, most of its users rely on and understand only about 10 percent of its functionality, not realizing the immensely useful other features that Metasploit offers. This course will enable students to master the 10 percent they currently rely on (applying it in a more comprehensive and safe manner), while unlocking the other 90 percent of features they can then apply to make their tests more effective. By attending this course, students will learn how to make a free tool achieve the power of many much more costly commercial tools.

- Jeff McJunkin

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