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.

    Topics
    • 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.

    Topics
    • 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

Important! Bring your own system configured according to these instructions.

A properly configured system is required to fully participate in this course. If you do not carefully read and follow these instructions, you will not be able to fully participate in hands-on exercises in your course. Therefore, please arrive with a system meeting all of the specified requirements.

Back up your system before class. Better yet, use a system without any sensitive/critical data. SANS is not responsible for your system or data.

MANDATORY SEC580 SYSTEM HARDWARE REQUIREMENTS

  • CPU: 64-bit Intel i5/i7 (8th generation or newer), or AMD equivalent. A x64 bit, 2.0+ GHz or newer processor is mandatory for this class.
  • CRITICAL: Apple systems using the M1/M2 processor line cannot perform the necessary virtualization functionality and therefore cannot in any way be used for this course.
  • BIOS settings must be set to enable virtualization technology, such as "Intel-VTx" or "AMD-V" extensions. Be absolutely certain you can access your BIOS if it is password protected, in case changes are necessary.
  • 8GB of RAM or more is required.
  • 60GB of free storage space or more is required.
  • At least one available USB 3.0 Type-A port. A Type-C to Type-A adapter may be necessary for newer laptops. Some endpoint protection software prevents the use of USB devices, so test your system with a USB drive before class.
  • Wireless networking (802.11 standard) is required. There is no wired Internet access in the classroom.

MANDATORY SEC580 HOST CONFIGURATION AND SOFTWARE REQUIREMENTS

  • Your host operating system must be the latest version of Windows 10, Windows 11, or macOS 10.15.x or newer.
  • Fully update your host operating system prior to the class to ensure you have the right drivers and patches installed.
  • Linux hosts are not supported in the classroom due to their numerous variations. If you choose to use Linux as your host, you are solely responsible for configuring it to work with the course materials and/or VMs.
  • Local Administrator Access is required. (Yes, this is absolutely required. Don't let your IT team tell you otherwise.) If your company will not permit this access for the duration of the course, then you should make arrangements to bring a different laptop.
  • You should ensure that antivirus or endpoint protection software is disabled, fully removed, or that you have the administrative privileges to do so. Many of our courses require full administrative access to the operating system and these products can prevent you from accomplishing the labs.
  • Any filtering of egress traffic may prevent accomplishing the labs in your course. Firewalls should be disabled or you must have the administrative privileges to disable it.
  • Download and install VMware Workstation Pro 16.2.X+ or VMware Player 16.2.X+ (for Windows 10 hosts), VMware Workstation Pro 17.0.0+ or VMware Player 17.0.0+ (for Windows 11 hosts), or VMWare Fusion Pro 12.2+ or VMware Fusion Player 11.5+ (for macOS hosts) prior to class beginning. If you do not own a licensed copy of VMware Workstation Pro or VMware Fusion Pro, 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. Also note that VMware Workstation Player offers fewer features than VMware Workstation Pro. For those with Windows host systems, Workstation Pro is recommended for a more seamless student experience.
  • On Windows hosts, VMware products might not coexist with the Hyper-V hypervisor. For the best experience, ensure VMware can boot a virtual machine. This may require disabling Hyper-V. Instructions for disabling Hyper-V, Device Guard, and Credential Guard are contained in the setup documentation that accompanies your course materials.
  • Download and install 7-Zip (for Windows Hosts) or Keka (for macOS hosts). These tools are also included in your downloaded course materials.

Your course media is delivered via download. The media files for class can be large. Many are in the 40-50GB range, with some over 100GB. 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 soon as you get the link. You will need your course media immediately on the first day of class. Do not wait until the night before class to start downloading these files.

Your course materials include a "Setup Instructions" document that details important steps you must take before you travel to a live class event or start an online class. It may take 30 minutes or more to complete these instructions.

If you have additional questions about the laptop specifications, please contact laptop_prep@sans.org

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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