Pittsburgh 2020

Overview

Understanding the attacker's perspective is key to successful web application penetration testing. The course begins by thoroughly examining web technology, including protocols, languages, clients, and server architectures, from the attacker's perspective. We also examine different authentication systems, including Basic, Digest, Forms, and Windows Integrated authentication, and discuss how servers use them and attackers abuse them. After authentication, we analyze the importance of encryption and HTTPS. Before leaving HTTPS, we dive into the infamous Heartbleed flaw and get our first taste of exploitation with a hands-on lab.

We then turn to the four steps that make up our process for conducting web application penetration tests: reconnaissance, mapping, discovery, and exploitation. On the first day, we review the fundamental principles of each phase and discuss how penetration testers can use them together as a cyclical in-depth attack process. We then cover the types of penetration testing and what pieces need to be part of a thorough, high-value pen test report. To complete the course day, we explore aspects of a vulnerable web application using Burp Suite.

Overview

The second day begins with the reconnaissance and mapping phases of a web app penetration test. Reconnaissance includes gathering publicly available information regarding the target application and organization, identifying the machines that support our target application, and building a profile of each server, including the operating system, specific software, and configuration. The discussion is underscored through several practical, hands-on labs in which we conduct reconnaissance against in-class targets.

In the mapping phase, we build a map or diagram of the application's pages and features. This phase involves identifying the components, analyzing the relationship between them, and determining how the pieces work together. We often discover configuration flaws in web application infrastructure components during the mapping phase. After discussion of these types of flaws, we use the Shellshock vulnerability as an opportunity to get deeper hands-on experience with Burp Suite, cURL, and manual exploitation techniques. We then dive deep into spidering/crawling web applications. Spidering represents a vital part of both the mapping phase and the overall penetration test.

Overview

This section continues to explore our methodology with the discovery phase. We build on the information identified during the mapping phase, exploring methods to find and verify vulnerabilities within the application. Students also begin to explore the interactions between the various vulnerabilities.

This course day dives deeply into vital manual testing techniques for vulnerability discovery. To facilitate manual testing, we kick off the day with an introduction to Python and a hands-on lab working with it.

In addition to custom scripts, we focus on developing in-depth knowledge of interception proxies for web application vulnerability discovery. A highlight of the day involves spending significant time working with both traditional and blind SQL injection flaws.

Throughout the discovery phase, we will explore both manual and automated methods of discovering vulnerabilities within applications and discuss the circumstances under which each is appropriate.

Overview

On day four, students continue exploring the discovery phase of the methodology. We cover methods to discover key vulnerabilities within web applications, such as Cross-Site Scripting (XSS) and Cross-Site Request Forgery (CSRF/XSRF). Manual discovery methods are employed during hands-on labs.

The course day will also include a detailed discussion of AJAX as we explore how it enlarges the attack surface leveraged by penetration testers. We also analyze how AJAX is affected by other vulnerabilities already covered in depth earlier in the course.

After detailing the various vulnerabilities and manual discovery methods, day four concludes with a review of various automated web application vulnerability scanners, to complement our previous coverage of manual techniques with scripting, ZAP, and the Burp Suite.

Overview

On the fifth day, we launch actual exploits against real-world applications, building on the previous three steps, expanding our foothold within the application, and extending it to the network on which it resides. As penetration testers, we specifically focus on ways to leverage previously discovered vulnerabilities to gain further access, highlighting the cyclical nature of the four-step attack methodology.

During our exploitation phase, we expand our use of tools such as ZAP and the Burp Suite, and complement them with further use of sqlmap, BeEF, the Browser Exploitation Framework, and Metasploit to help craft exploits against various web applications. We launch SQL injection, Cross-Site Scripting (XSS), and Cross-Site Request Forgery attacks, amongst others. In class we exploit these flaws to perform data theft, hijack sessions, steal passwords, get shells, pivot against connected networks, and much more. Through various forms of exploitation, the student gains a keen understanding of the potential business impact of these flaws to an organization.