SEC660: Advanced Penetration Testing, Exploit Writing, and Ethical Hacking

Overview

Section one serves as an advanced network attack module, building on knowledge gained from SEC560: Network Penetration Testing and Ethical Hacking. The focus will be on obtaining access to the network; manipulating the network to gain an attack position for eavesdropping and attacks, and for exploiting network devices; leveraging weaknesses in network infrastructure; and taking advantage of client frailty.

Topics

• Bypassing network access/admission control (NAC)
• Impersonating devices with admission control policy exceptions
• Custom network protocol manipulation with Ettercap and custom filters
• Multiple techniques for performing network-based tampering
• IPv6 for penetration testers
• Exploiting OSPF authentication to inject malicious routing updates
• Overcoming TLS/SSL transport encryption security with SSL-stripping

Overview

Section two starts by taking a tactical look at techniques that penetration testers can use to investigate and exploit common cryptography mistakes. We begin by building some fundamental knowledge on how ciphers operate, without getting bogged down in complex mathematics. Then we move on to techniques for identifying, assessing, and attacking real-world crypto implementations. We finish the module with lab exercises that allow students to practice their newfound crypto attack skill set against reproduced real-world application vulnerabilities.

The section continues with advanced techniques but focuses more on post exploitation tasks. We leverage an initial foothold to further exploit the rest of the network. We abuse allowed features to escape restricted environments. First we will build up knowledge of local restrictions on hosts. Once we establish a set of possible restrictions, we leverage that knowledge to circumvent them. We will cover the core components that restrict the desktop and a variety of escape possibilities. The Kiosk escape exercise is a perfect, real-world demonstration of the risks of relying on obfuscation and deny controls to thwart attacks.

As a major factor in post exploitation, we cover both exploiting administrator's use of PowerShell and PowerShell attack tools. We'll use specialized and alternative tools to escalate privileges, pivot, and deliver additional payloads. The section ends with a challenging boot camp exercise against a full network environment comprised of a variety of modern, representative, and fully patched systems with no obvious remote vulnerabilities.

Topics

• Pen testing cryptographic implementations
• Exploiting CBC bit flipping vulnerabilities
• Exploiting hash length extension vulnerabilities
• Delivering malicious operating systems to devices using network booting and PXE
• PowerShell as a victim
• PowerShell as an attacker
• Post Exploitation with PowerShell and alternatives
• Escaping Software Restrictions
• Two-hour Capture the Flag exercise against an enterprise Data Loss Prevention solution

Overview

Section 3 brings together the multiple skill sets needed for creative analysis in penetration testing. We start by discussing product security testing. The section continues with a focus on how to leverage Python as a penetration tester - the aim is to help students unfamiliar with Python start modifying scripts to add their own functionality, while also helping seasoned Python scripters improve their skills. Once we leverage the Python skills in creative lab exercises, we move on to leveraging Scapy for custom network targeting and protocol manipulation. Using Scapy, we examine techniques for transmitting and receiving network traffic beyond what canned tools can accomplish, including IPv6. Next, we take a look at network protocol and file format fuzzing. We leverage fuzzing to target both common network protocols and popular file formats for bug discovery. We use hands-on exercises to develop custom protocol fuzzing grammars to discover bugs in popular software. Finally, we carefully discuss the concept of code coverage and how it goes hand-in-hand with fuzzing. We will conduct a lab using the DynamRio instruction manipulation library and IDA Pro to demonstrate the techniques discussed.

Topics

• Becoming familiar with Python types
• Leveraging Python modules for real-world pen tester tasks
• Manipulating stateful protocols with Scapy
• Using Scapy to create a custom wireless data leakage tool
• Product security testing
• Using Sulley for quick protocol mutation fuzzing
• Optimizing your fuzzing time with smart target selection
• Automating target monitoring while fuzzing with Sulley
• Source code-assisted binary fuzzing and code coverage measurement using AFL++
• Block-based code coverage techniques using DynamoRio

Overview

Section four begins by walking through memory from an exploitation perspective as well as introducing x86 and x86-64 assembler and linking and loading. These topics are important for anyone performing penetration testing at an advanced level. Processor registers are directly manipulated by testers and must be intimately understood. Disassembly is a critical piece of testing and will be used throughout the remainder of the course. We will take a look at the Linux OS from an exploitation perspective and discuss privilege escalation. We continue by describing how to look for SUID programs and other likely points of vulnerabilities and misconfigurations. The material will focus on techniques that are critical to performing penetration testing on Linux applications.

We then go heavily into stack overflows on Linux to gain privilege escalation and code execution. We will first cover using a debugger to expose weak passwords. Then we will go over redirection of program execution and, finally, code execution. Techniques such as return to buffer and return to C library (ret2libc) will be covered, as well as an introduction to return-oriented programming. The remainder of the section takes students through techniques used to defeat or bypass OS protections such as stack canaries and address space layout randomization (ASLR). The goal of this section is to expose students to common obstacles on modern Linux-based systems.

Topics

• Stack memory management and allocation on the Linux OS
• Disassembling a binary and analyzing x86/x86-64 assembly code
• Performing symbol resolution on the Linux OS
• Identifying vulnerable programs
• Code execution redirection
• Identifying and analyzing stack-based overflows on the Linux OS
• Performing return-to-libc (ret2libc) attacks on the stack
• Return-oriented programming
• Defeating stack protection on the Linux OS
• Defeating ASLR on the Linux OS

Overview

Section five starts off covering the OS security features (ASLR, DEP, etc.) added to the Windows OS over the years as well as Windows-specific constructs, such as the process environment block (PEB), structured exception handling (SEH), thread information block (TIB), and the Windows application programming interfaces (API). Differences between Linux and Windows will be covered. These topics are critical in assessing Windows-based applications. We then focus on stack-based attacks against programs running on the Windows OS. After finding a vulnerability in an application, the student will work with Immunity Debugger to turn the bug into an opportunity for code execution and privilege escalation. Advanced stack-based techniques such as disabling data execution prevention (DEP) are covered. Client-side exploitation will be introduced, as it is a highly common area of attack. We continue with the topic of return-oriented programming (ROP), demonstrating the technique against a vulnerable application, while looking at defeating hardware DEP and address space layout randomization (ASLR) and Windows 10. Finally, we will take a quick look at shellcode and the differences between shellcode on Linux and Windows, followed by a ROP challenge.

Topics

• The state of Windows OS protections on the Windows OS
• Understanding common Windows constructs
• Stack exploitation on Windows
• Defeating OS protections added to Windows
• Creating a Metasploit module
• Advanced stack-smashing on Windows
• Using ROP
• Building ROP chains to defeat DEP and bypass ASLR
• Windows 10 exploitation
• Client-side exploitation
• Windows Shellcode

Overview

This section will serve as a real-world challenge for students by requiring them to utilize skills they have learned throughout the course, think outside the box, and solve a range of problems from simple to complex. A web server scoring system and Capture the Flag engine will be provided to score students as they capture flags. More difficult challenges will be worth more points. In this offensive exercise, challenges range from local privilege escalation to remote exploitation on both Linux and Windows systems, as well as networking attacks and other challenges related to the course material.