Mentor Session - SEC 560 Ethical Hacking Washington DC Metro

Security vulnerabilities, such as weak configurations, unpatched systems, and botched architectures, continue to plague organizations. Enterprises need people who can find these flaws in a professional manner to help eradicate them from our infrastructures. Lots of people claim to have penetration testing, ethical hacking, and security assessment skills, but precious few can apply these skills in a methodical regimen of professional testing to help make an organization more secure. This class covers the ingredients for successful network penetration testing to help attendees improve their enterprise's security stance.

We address detailed pre-test planning, including setting up an effective penetration testing infrastructure and establishing ground rules with the target organization to avoid surprises and misunderstanding. Then, we discuss a time-tested methodology for penetration and ethical hacking across the network, evaluating the security of network services and the operating systems behind them.

Attendees will learn how to perform detailed reconnaissance, learning about a target's infrastructure by mining blogs, search engines, and social networking sites. We'll then turn our attention to scanning, experimenting with numerous tools in hands-on exercises. Our exploitation phase will include the use of exploitation frameworks, stand-alone exploits, and other valuable tactics, all with hands-on exercises in our lab environment. The class also discusses how to prepare a final report, tailored to maximize the value of the test from both a management and technical perspective. The final portion of the class includes a comprehensive hands-on exercise, conducting a penetration test against a hypothetical target organization, following all of the steps.

The course also describes the limitations of penetration testing techniques and other practices that can be used to augment penetration testing to find vulnerabilities in architecture, policies, and processes. We also address how penetration testing should be integrated as a piece of a comprehensive enterprise information security program.

This SANS course differs from other penetration testing and ethical hacking courses in several important ways:

Laptop Info

IMPORTANT - BRING YOUR OWN LAPTOP WITH WINDOWS

To get the most value out of the course, students are required to bring their own laptop so that they can connect directly to the workshop network that we will create. It is the students' responsibility to make sure that the system is properly configured with all drivers necessary to connect to an Ethernet network.

Some of the course exercises are based on Windows, while others focus on Linux. VMware Player or VMware Workstation is required for the class. If you plan to use a Macintosh, please make sure you bring VMware Fusion, along with a Windows guest virtual machine.

Windows

You are required to bring Windows 7 (Professional or Ultimate), Windows Vista (Business or Ultimate), Windows XP Pro, or Windows 2003 or 2008 Server, either a real system or a virtual machine. Windows 7 Home, Windows Vista Home, Windows XP Home, and Windows 2000 (all versions) will NOT work for the class as they do not include all of the built-in capabilities we need for comprehensive analysis of the system.

The course includes a VMware image file of a guest Linux system that is larger than 2 GB. Therefore, you need a file system with the ability to read and write files that are larger than 2 GB, such as NTFS on a Windows machine.

IMPORTANT NOTE:You will also be required to disable your anti-virus tools temporarily for some exercises, so make sure you have the anti-virus administrator permissions to do so. DO NOT plan on just killing your anti-virus service or processes because most anti-virus tools still function even when their associated services and processes have been terminated. For many enterprise-managed clients, disabling your anti-virus tool may require a different password than the Administrator account password. Please bring that administrator password for your anti-virus tool.

Enterprise VPN clients may interfere with the network configuration required to participate in the class. If your system has an enterprise VPN client installed, you may need to uninstall it for the exercises in class.

VMware

You will use VMware to run Windows and Linux operating systems simultaneously when performing exercises in class. You must have either the free VMware Player 3 or later or the commercial VMware Workstation 6 or later installed on your system prior to coming to class. You can download VMware Player for free here.

Alternatively, if you want a more flexible and configurable tool, you can download a free 30-day trial copy of VMware Workstation here. VMware will send you a time- limited license number for VMware Workstation if you register for the trial at their Web site. No license number is required for VMware Player.

We will give you a DVD full of attack tools to experiment with during the class and take home for later analysis. We will also provide a Linux image with all of our tools pre-installed that runs within VMware Player or VMware Workstation.

Linux

You do not need to bring a Linux system if you plan to use our Linux image in VMware. However, you are required to bring VMware Workstation or VMware Player. The class does not support VirtualPC or other non-VMware virtualization products.

Mandatory Laptop Hardware Requirements

• x86- or x64-compatible 1.5 GHz CPU Minimum or higher
• DVD Drive (not a CD drive)
• 2 GigaByte RAM minimum with 4 GB or higher recommended
• Ethernet adapter (A wired connection is required in class. If your laptop supports only wireless, please make sure to bring an Ethernet adapter with you.)
• 5 GigaByte available hard drive space
• Any Service Pack level is acceptable for Windows XP Pro, 2003, Vista, or Win7

During the workshop, you will be connecting to one of the most hostile networks on planet Earth! Your laptop might be attacked. Do not have any sensitive data stored on the system. SANS is not responsible for your system if someone in the class attacks it in the workshop.

By bringing the right equipment and preparing in advance, you can maximize what you'll see and learn as well as have a lot of fun.

Section 1: Network Penetration Testing: Planning, Scoping, and Recon

6 CPE/CMU Credits

Successful professional penetration testers and ethical hackers must carefully prepare before their projects, and this detailed session covers that strategies and tactics for doing so effectively. We cover building a penetration testing and ethical hacking infrastructure that includes the appropriate hardware, software, network infrastructure, and test tools arsenal, with specific low-cost recommendations for maximizing your effectiveness on a limited budget. This portion of the course also describes how to plan the specifics of a test, carefully scoping the project and defining the rules of engagement with target environment personnel. We survey the various legal issues associated with the penetration testing and ethical hacking craft in various countries around the world.

After this detailed analysis of preparation, the session changes topics to deal with reconnaissance, the initial phase of most penetration tests and ethical hacking projects. We'll look at maximizing the usefulness of information from public sources, including detailed and advanced DNS interrogations, whois look-ups, and late-breaking search engine vulnerability finding tools. We'll also look at emerging recon suites and how we can best position them in our testing regimens.

• The mindset of a professional penetration tester and ethical hacker
• Types of penetration tests and ethical hacking projects, with an overview of various testing methodologies
• Limitations of penetration testing, and how testing fits into an overall security program
• Building a testing infrastructure, including practical recommendations for selecting hardware, tools, and network infrastructures
• Defining rules of engagement and scoping a project
• Exercise: Dealing with an ambiguous pen test RFP
• Legal issues with penetration testing around the world
• Reporting - how to achieve business focus and technical depth
• A pen tester's tool chest of reconnaissance resources
• Whois lookups - maximizing the usefulness of registrars, Autonomous System Numbers, etc.
• DNS lookups with nslookup, dig, Sensepost's BiLE, etc.
• Search engine vulnerability-finding tools: Aura, Wikto, EvilAPI, and more

Section 2: Network Penetration Testing: Scanning

6 CPE/CMU Credits

This component of the course focuses on the vital task of scanning a target environment, creating a comprehensive inventory of machines and then evaluating those systems to find potential vulnerabilities. We'll look at some of the most useful scanning tools freely available today, experimenting with them in our hands-on lab. Because vulnerability-scanning tools inevitably give us false positives, we'll conduct an exercise on false-positive reduction, analyzing several methods for getting inside of what our tools are telling us to ensure the veracity of our findings. Our hands-on exercises include the creative use of packet crafting to measure the fine-grained behavior of target machines, all while watching the action from a custom-configured sniffer. We also look at some of the late-breaking features of popular tools, including the latest Nmap Scripting Engine capabilities.

• Types of scans - Network sweeps, network tracing, port scans, OS fingerprinting, version scans, and vulnerability scans
• Overall scanning tips - tcpdump for the pen tester, protocol anomalies, and troubleshooting
• Exercise: Packet crafting for the pen tester with Hping3 and monitoring with tcpdump
• Network tracing in-depth with traditional traceroute and exotic network mapping techniques
• Port scanning in-depth with the latest Nmap features
• Exercise: Finding vulnerabilities with the Nmap Scripting Engine (NSE)
• OS Fingerprinting
• Version Scanning with Nmap and Amap
• Exercise: False positive reduction
• Vulnerability Scanning
• Exercise: Comprehensive vulnerability scanner configuration

Section 3: Network Penetration Testing: Exploitation and Post Exploitation

6 CPE/CMU Credits

In this section, we look at the many kinds of exploits that a penetration tester or ethical hacker can use to compromise a target machine. We'll analyze in detail the differences between server-side, client-side, and local privilege escalation exploits, exploring some of the most useful recent exploits in each category. We'll see how these exploits are packaged in frameworks like Metasploit. We'll go over some of the more advanced Metasploit options, including its mighty Meterpreter, discussing some of the best features in this really powerful payload that are hugely helpful for penetration testers and ethical hackers.

We'll also look at some of the common pitfalls that we face when running exploits, as well as methods for mitigating, dodging, or even eliminating those issues. Finally, we'll zoom in on Windows. With its 80+% market share and regular discovery of vulnerabilities and release of exploits, the culmination of exploitation is often a command shell on a Windows box. We'll see how to maximize the effectiveness of that access, activating RDP, VNC, and installing SSH, all from a command prompt. Almost every topic covered in this session includes hands-on exercises to give attendees practical experience in using these techniques. Topics include:

• Exploit categories - server-side, client-side, and local privilege escalation
• Comprehensive Metasploit Framework coverage - exploits, stagers, stages and how penetration testers can get the most value out of subtle but powerful features
• Exercise: Using Metasploit to get remote shell via server-side flaw
• The Metepreter in depth, including file, process, and network interactions and the priv module
• Exercise: Advanced usage of the Meterpreter payload
• Exercise: Non-Metasploit exploits - using a raw exploit to gain access
• The dilemma of command shell vs. terminal access
• Exercise: Bypassing the dilemma on Linux/Unix and Windows
• Installing and activating VNC, RDP, sshd, and telnet services from a command shell
• Moving files with exploits cross platform
• Windows command line kung fu specifically targeted at pen testers: making ping sweepers, port scanners, reverse DNS lookup tools, and password guessers at the command-line
• Exercise: Challenging your kung fu
• Exercise: Making Windows run commands remotely with psexec, sc, and wmic

Section 4: Network Penetration Testing: Password Attacks

6 CPE/CMU Credits

This component of the course turns our attention to password attacks, analyzing password guessing, password cracking, and pass-the-hash techniques in depth. Because passwords remain the dominant authentication scheme of most enterprises, professional penetration testers and ethical hackers need to understand how to find password weaknesses in a target environment. We'll go over numerous tips based on real-world experience to help penetration testers and ethical hackers maximize the effectiveness of their password attacks. We'll cover one of the best automated password-guessing tools available today, THC Hydra, and run it against target machines to guess Windows SMB and Linux SSH passwords. We'll then zoom in on the password representation formats for most major operating systems, discussing various cracking tools in-depth.

We'll do exercises in which we.ll patch the John the Ripper password cracker so that it can support NT hashes, and then compare its performance when compiled for different kinds of processor types. We'll look at the amazingly full-featured Cain tool, running it to crack sniffed Windows authentication messages. We'll see how Rainbow tables work to make password cracking much more efficient, and run a hands-on exercise using the technique. And, we'll finish the day with a lively discussion of a really powerful attack vector that doesn't require password cracking, but instead uses captured encrypted credentials to access Windows machines directly, in a so-called "pass-the-hash" attack, using customized Samba code for a hands-on exercise illustrating the technique. Specific topics include:

• The primacy of passwords
• Password attack tips: Making the most of password attacks in a safe and efficient manner
• Account lockout and strategies for avoiding it
• Password Guessing with THC-Hydra
• Exercise: Using THC-Hydra and throttling guesses to avoid problems
• Password representation formats in depth: Windows LANMAN, NT, NTLMv1, NTLMv2, Unix DES, and Linux MD5
• Exercise: Dumping Windows hashes with fgdump, via an instrumented Netcat relay
• John the Ripper features for penetration testers
• Exercise: Patching John for NT hashes, comparing MMX vs. non-MMX performance, and cracking LANMAN, NT, and Linux MD5 representations
• Cain: The pen tester's dream tool
• Exercise: Cain sniffing and cracking NTLMv1 challenge/response exchanges
• Rainbow table attacks in depth: How the tables work and how you can use them for more efficiency
• Exercise: Using Ophcrack, booting ISOs via a VMX file, and applying Rainbow Tables
• Pass-the-hash attacks against Windows: Using hashes without even cracking a password
• Exercise: Pass-the-hash hands-on against Windows via Foofus patches for Samba

Section 5: Network Penetration Testing: Wireless and Web Apps

6 CPE/CMU Credits

With the increasing use of wireless networking technologies, professional penetration testers and ethical hackers are often called upon to evaluate these infrastructures for flaws. This section of the course describes methodologies for finding common wireless weaknesses, including misconfigured access points, application of weak security protocols, and the improper configuration of stronger security technologies.

The second half of this session focuses on web application penetration testing, looking for the numerous flaws that impact commercial and homegrown web apps. Attendees will work hands-on with tools that can find Cross-Site Scripting (XSS) and Cross-Site Request Forgery (XSRF) flaws, experimenting with each in a hands-on exercise. We'll look at command injection and directory traversal flaws, experimenting with them in hands-on exercises. Finally, the session deals with the sometimes devastating SQL injection flaws and session cloning issues that have resulted in significant website compromises.

• Web application scanning and exploitation tools
• Exercise: Scanning a web app for flaws
• Web application manipulation tools
• Exercise: Using Paros Proxy to target a web app
• The myriad of web application injection attacks
• Exercise: XSRF, XSS, session cloning, and command injection hands-on
• Building a wireless testing rig
• Finding unsecured access points and peer-to-peer systems
• Identifying common wireless misconfigurations
• Wireless protocol problems and how a penetration tester can exploit them

Section 6: Penetration Testing Workshop & Capture the Flag Event

6 CPE/CMU Credits

This lively session represents the culmination of the network penetration testing and ethical hacking course, where attendees will apply the skills that they've mastered throughout all the other sessions in a hands-on workshop. The rest of the course covers the overall process for successful testing, with a series of hands-on exercises individually illustrating each point. But here, in this final workshop, all of the exercises converge into an overall network penetration-testing workout. Operating as part of a team, attendees will conduct a penetration test of a target environment in the classroom, following all of the steps of a professional penetration tester and ethical hacker. You'll have to scan for flaws, use exploits, unravel technical challenges, and dodge firewalls, all the while analyzing and documenting your results in a comprehensive manner. Teams will compete with each other to be the first to win the Capture the Flag game that is the centerpiece of this workshop.

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