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Abusing HTTP Misconfigurations

This module covers three common HTTP vulnerabilities: Web Cache Poisoning, Host Header Vulnerabilities, and Session Puzzling or Session Variable Overloading. These vulnerabilities can arise on the HTTP level due to web server misconfigurations, other systems that have to be considered during real-world deployment such as web caches, or coding mistakes in the web application. We will cover how to identify, exploit, and prevent each of these vulnerabilities.

4.68

Created by vautia

Hard Offensive

Summary

As the security awareness of administrators is increasing, beginner-level vulnerabilities and low-hanging fruits are (hopefully) often detected and avoided, at least for larger internet-facing web applications. However, more advanced vulnerabilities that arise from the deployment of web applications in real-world settings are often forgotten. During the actual deployment of a web application in a real-world setting we have to consider more factors than just the web application itself. That includes the web server (and potentially misconfigurations or default options that administrators might be unaware of) and intermediary systems such as web caches. All these factors combined create a complex environment of different configurations that leave room for vulnerabilities. This module covers three such vulnerabilities: web cache poisoning which is often the result of discrepancies between web caches and the web application, host header attacks which can be caused by misconfigured web servers and flaws in the web application, and session puzzling or session variable overloading which arises from improper handling of session variables in the web application.

In more detail, this module covers the following:

  • Web Cache Poisoning:
    • What is a web cache and how does it work?
    • How can web caches be configured?
    • What are keyed & unkeyed parameters and how to identify them?
    • Exploiting basic web cache poisoning vulnerabilities
    • Using advanced techniques to exploit web cache poisoning vulnerabilities
  • Host Header Attacks:
    • What is the Host header and why is it needed?
    • What are override headers?
    • Exploiting host header vulnerabilities such as password reset poisoning
    • Bypassing flawed host header validation
  • Session Puzzling:
    • What are session variables and why are they needed?
    • Exploiting weak session IDs
    • Exploiting session puzzling due to insecure defaults
    • Exploiting session puzzling due to common session variables
    • Exploiting session puzzling due to premature session population

CREST CCT APP-related Sections:

  • All sections

CREST CCT INF-related Sections:

  • All sections

This module is broken into sections with accompanying hands-on exercises to practice each of the tactics and techniques we cover. The module ends with a practical hands-on skills assessment to gauge your understanding of the various topic areas.

You can start and stop the module at any time and pick up where you left off. There is no time limit or "grading", but you must complete all of the exercises and the skills assessment to receive the maximum number of cubes and have this module marked as complete in any paths you have chosen.

As you work through the module, you will see example commands and command output for the various topics introduced. It is worth reproducing as many of these examples as possible to reinforce further the concepts presented in each section. You can do this in the PwnBox provided in the interactive sections or your virtual machine.

A firm grasp of the following modules can be considered a prerequisite for the successful completion of this module:

  • Web Requests
  • Introduction to Web Applications
  • Cross-Site Scripting (XSS)

Introduction to HTTP Misconfigurations

With billions of devices relying on it every day, HTTP is one of the most utilized protocols on the Internet. Today, web application security constitutes one the most vital parts of Cyber Security, as it is important to not only look at a web application discretely, but rather holistically in a real-world deployment which includes systems such as web servers and web caches that introduce additional complexity and therefore attack surface.

In this module, we will cover three HTTP attacks that are common in modern web applications. We will discuss these attacks in detail, including how to detect, exploit, and prevent these types of attacks.

Web services that are used by many users utilize web caches to improve performance by reducing the load on the web server. Web caches sit between the client and the web server. They store resources locally after obtaining them from the web server, such that they can serve them from local storage if the same resource is requested again. Thus, the resources do not need to be requested from the web server, reducing the load on the web server. Vulnerabilities that can arise when web servers utilize web caches will be discussed in this module.

The HTTP Host header is present in any HTTP request since HTTP/1.1. It specifies the hostname and potentially the port of the server to which the request is being sent. When web servers host multiple web applications, the host header is used to determine which web application is targeted by the request and the response is served accordingly. In this module, we will discuss vulnerabilities that can arise from improper handling of the host header in the web application.

Since HTTP is a stateless protocol, sessions are required to provide context for requests. For instance, HTTP sessions are used to perform authenticated actions without having to send credentials in every request. The web application typically identifies the user by their session ID, which the user provides in a session cookie in most cases. On the server side, information about the user is stored in the session variables associated with the corresponding session ID. The last part of this module focuses on vulnerabilities that result from improper handling of session variables.

HTTP Attacks

Web Cache Poisoning

The first HTTP attack discussed in this module is Web Cache Poisoning. This attack exploits misconfigurations in web caches in combination with other vulnerabilities in the underlying web application to target unknowing users. Depending on the specific vulnerability, it might be sufficient for a victim to simply access the targeted website to be exploited. Web cache poisoning can also lead to otherwise unexploitable vulnerabilities being weaponized to target a huge number of potential victims.

Host Header Attacks

The second type of attacks discussed in this module are Host Header Attacks. The HTTP host header contains the host of the accessed domain and is used to tell the server which domain a user wants to access. This is required for instances where a single server serves multiple domains or subdomains so that the server can identify the targeted application. Host header attacks exploit vulnerabilities in the handling of the host header. More specifically, if a web application uses the host header for authorization checks or to construct absolute links, an attacker may be able to manipulate the host header to bypass these checks or force the construction of malicious links.

Session Puzzling

The third and final attack covered in this module is Session Puzzling. Since HTTP is a stateless protocol, session variables are required to keep track of a wide variety of actions commonly performed in web applications, including authentication. Session puzzling is a vulnerability that results from improper handling of session variables and can lead to authentication bypasses or account takeover. In particular, session puzzling can be the result of the re-use of the same session variable in different processes, the premature population of session variables, or insecure default values for session variables.

Let's get started by discussing the first of these attacks in the next section.

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Sections

Relevant Paths

This module progresses you towards the following Paths

CREST CCT APP Preparation

CREST CCT APP Preparation

This is a skill path to prepare you for CREST's CCT APP exam. The following CCT APP syllabus areas (IDs) are covered: A1, A2, A3, A4, A5, B1, B4, B5, B6, B8, B9, B13, B14, C1, C2, C3, C4, D1, D2, E1, E2, E3, E4, E5, E9, F1, F2, F3, F4, F5, F6, F7, F8, F9, G1, G2, G4, G5, G6, G7, G8, G9, H1, H2, H3, H4, H5, H6, H7, H8, H9, H10, H11, H12, H13, I1, I2, I3, I4, I5, I6, I7, I8, I9, I10, I11, I12, J1, J2, J3. Take your time to complete all related sections and when you are ready you can book your CREST exam through the following link. https://www.crest-approved.org/certification-careers/crest-certifications/crest-certified-web-application-tester/

Medium Path Sections 750 Sections
Required: 4980
Reward: +1100
Path Modules
Introduction to Networking
Fundamental
Path Sections 21 Sections
Reward: +10
As an information security professional, a firm grasp of networking fundamentals and the required components is necessary. Without a strong foundation in networking, it will be tough to progress in any area of information security. Understanding how a network is structured and how the communication between the individual hosts and servers takes place using the various protocols allows us to understand the entire network structure and its network traffic in detail and how different communication standards are handled. This knowledge is essential to create our tools and to interact with the protocols.
Web Requests
Fundamental
Path Sections 8 Sections
Reward: +10
This module introduces the topic of HTTP web requests and how different web applications utilize them to communicate with their backends.
Introduction to Web Applications
Fundamental
Path Sections 17 Sections
Reward: +10
In the Introduction to Web Applications module, you will learn all of the basics of how web applications work and begin to look at them from an information security perspective.
Linux Fundamentals
Fundamental
Path Sections 30 Sections
Reward: +10
This module covers the fundamentals required to work comfortably with the Linux operating system and shell.
Windows Fundamentals
Fundamental
Path Sections 14 Sections
Reward: +10
This module covers the fundamentals required to work comfortably with the Windows operating system.
Introduction to Windows Command Line
Easy
Path Sections 23 Sections
Reward: +10
As administrators and Pentesters, we may not always be able to utilize a graphical user interface for the actions we need to perform. Introduction to Windows Command Line aims to introduce students to the wide range of uses for Command Prompt and PowerShell within a Windows environment. We will cover basic usage of both key executables for administration, useful PowerShell cmdlets and modules, and different ways to leverage these tools to our benefit.
Intro to Network Traffic Analysis
Medium
Path Sections 15 Sections
Reward: +10
Network traffic analysis is used by security teams to monitor network activity and look for anomalies that could indicate security and operational issues. Offensive security practitioners can use network traffic analysis to search for sensitive data such as credentials, hidden applications, reachable network segments, or other potentially sensitive information "on the wire." Network traffic analysis has many uses for attackers and defenders alike.
Penetration Testing Process
Fundamental
Path Sections 15 Sections
Reward: +10
This module teaches the penetration testing process broken down into each stage and discussed in detail. We will cover many aspects of the role of a penetration tester during a penetration test, explained and illustrated with detailed examples. The module also covers pre-engagement steps like the criteria for establishing a contract with a client for a penetration testing engagement.
Network Enumeration with Nmap
Easy
Path Sections 12 Sections
Reward: +10
Nmap is one of the most used networking mapping and discovery tools because of its accurate results and efficiency. The tool is widely used by both offensive and defensive security practitioners. This module covers fundamentals that will be needed to use the Nmap tool for performing effective network enumeration.
Footprinting
Medium
Path Sections 21 Sections
Reward: +20
This module covers techniques for footprinting the most commonly used services in almost all enterprise and business IT infrastructures. Footprinting is an essential phase of any penetration test or security audit to identify and prevent information disclosure. Using this process, we examine the individual services and attempt to obtain as much information from them as possible.
Information Gathering - Web Edition
Easy
Path Sections 19 Sections
Reward: +20
This module equips learners with essential web reconnaissance skills, crucial for ethical hacking and penetration testing. It explores both active and passive techniques, including DNS enumeration, web crawling, analysis of web archives and HTTP headers, and fingerprinting web technologies.
Vulnerability Assessment
Easy
Path Sections 17 Sections
Reward: +10
This module introduces the concept of Vulnerability Assessments. We will review the differences between vulnerability assessments and penetration tests, how to carry out a vulnerability assessment, how to interpret the assessment results, and how to deliver an effective vulnerability assessment report.
File Transfers
Medium
Path Sections 10 Sections
Reward: +10
During an assessment, it is very common for us to transfer files to and from a target system. This module covers file transfer techniques leveraging tools commonly available across all versions of Windows and Linux systems.
Shells & Payloads
Medium
Path Sections 17 Sections
Reward: +10
Gain the knowledge and skills to identify and use shells & payloads to establish a foothold on vulnerable Windows & Linux systems. This module utilizes a fictitious scenario where the learner will place themselves in the perspective of a sysadmin trying out for a position on CAT5 Security's network penetration testing team.
Using the Metasploit Framework
Easy
Path Sections 15 Sections
Reward: +10
The Metasploit Framework is an open-source set of tools used for network enumeration, attacks, testing security vulnerabilities, evading detection, performing privilege escalation attacks, and performing post-exploitation.
Password Attacks
Medium
Path Sections 22 Sections
Reward: +10
Passwords are still the primary method of authentication in corporate networks. If strong password policies are not in place, users will often opt for weak, easy-to-remember passwords that can often be cracked offline and used to further our access. We will encounter passwords in many forms during our assessments. We must understand the various ways they are stored, how they can be retrieved, methods to crack weak passwords, ways to use hashes that cannot be cracked, and hunting for weak/default password usage.
Attacking Common Services
Medium
Path Sections 19 Sections
Reward: +20
Organizations regularly use a standard set of services for different purposes. It is vital to conduct penetration testing activities on each service internally and externally to ensure that they are not introducing security threats. This module will cover how to enumerate each service and test it against known vulnerabilities and exploits with a standard set of tools.
Cracking Passwords with Hashcat
Medium
Path Sections 14 Sections
Reward: +20
This module covers the fundamentals of password cracking using the Hashcat tool.
Introduction to Active Directory
Fundamental
Path Sections 16 Sections
Reward: +10
Active Directory (AD) is present in the majority of corporate environments. Due to its many features and complexity, it presents a vast attack surface. To be successful as penetration testers and information security professionals, we must have a firm understanding of Active Directory fundamentals, AD structures, functionality, common AD flaws, misconfigurations, and defensive measures.
Pivoting, Tunneling, and Port Forwarding
Medium
Path Sections 18 Sections
Reward: +20
Once a foothold is gained during an assessment, it may be in scope to move laterally and vertically within a target network. Using one compromised machine to access another is called pivoting and allows us to access networks and resources that are not directly accessible to us through the compromised host. Port forwarding accepts the traffic on a given IP address and port and redirects it to a different IP address and port combination. Tunneling is a technique that allows us to encapsulate traffic within another protocol so that it looks like a benign traffic stream.
Active Directory Enumeration & Attacks
Medium
Path Sections 36 Sections
Reward: +20
Active Directory (AD) is the leading enterprise domain management suite, providing identity and access management, centralized domain administration, authentication, and much more. Due to the many features and complexity of AD, it presents a large attack surface that is difficult to secure properly. To be successful as infosec professionals, we must understand AD architectures and how to secure our enterprise environments. As Penetration testers, having a firm grasp of what tools, techniques, and procedures are available to us for enumerating and attacking AD environments and commonly seen AD misconfigurations is a must.
Linux Privilege Escalation
Easy
Path Sections 28 Sections
Reward: +20
Privilege escalation is a crucial phase during any security assessment. During this phase, we attempt to gain access to additional users, hosts, and resources to move closer to the assessment's overall goal. There are many ways to escalate privileges. This module aims to cover the most common methods emphasizing real-world misconfigurations and flaws that we may encounter in a client environment. The techniques covered in this module are not an exhaustive list of all possibilities and aim to avoid extreme "edge-case" tactics that may be seen in a Capture the Flag (CTF) exercise.
Windows Privilege Escalation
Medium
Path Sections 33 Sections
Reward: +20
After gaining a foothold, elevating our privileges will provide more options for persistence and may reveal information stored locally that can further our access in the environment. Enumeration is the key to privilege escalation. When you gain initial shell access to the host, it is important to gain situational awareness and uncover details relating to the OS version, patch level, any installed software, our current privileges, group memberships, and more. Windows presents an enormous attack surface and, being that most companies run Windows hosts in some way, we will more often than not find ourselves gaining access to Windows machines during our assessments. This covers common methods while emphasizing real-world misconfigurations and flaws that we may encounter during an assessment. There are many additional "edge-case" possibilities not covered in this module. We will cover both modern and legacy Windows Server and Desktop versions that may be present in a client environment.
Using Web Proxies
Easy
Path Sections 15 Sections
Reward: +20
Web application penetration testing frameworks are an essential part of any web penetration test. This module will teach you two of the best frameworks: Burp Suite and OWASP ZAP.
Attacking Web Applications with Ffuf
Easy
Path Sections 13 Sections
Reward: +10
This module covers the fundamental enumeration skills of web fuzzing and directory brute forcing using the Ffuf tool. The techniques learned in this module will help us in locating hidden pages, directories, and parameters when targeting web applications.
Login Brute Forcing
Easy
Path Sections 13 Sections
Reward: +20
The module contains an exploration of brute-forcing techniques, including the use of tools like Hydra and Medusa, and the importance of strong password practices. It covers various attack scenarios, such as targeting SSH, FTP, and web login forms.
Cross-Site Scripting (XSS)
Easy
Path Sections 10 Sections
Reward: +20
Cross-Site Scripting (XSS) vulnerabilities are among the most common web application vulnerabilities. An XSS vulnerability may allow an attacker to execute arbitrary JavaScript code within the target's browser and result in complete web application compromise if chained together with other vulnerabilities. This module will teach you how to identify XSS vulnerabilities and exploit them.
Session Security
Medium
Path Sections 14 Sections
Reward: +20
Maintaining and keeping track of a user's session is an integral part of web applications. It is an area that requires extensive testing to ensure it is set up robustly and securely. This module covers the most common attacks and vulnerabilities that can affect web application sessions, such as Session Hijacking, Session Fixation, Cross-Site Request Forgery, Cross-Site Scripting, and Open Redirects.
SQL Injection Fundamentals
Medium
Path Sections 17 Sections
Reward: +10
Databases are an important part of web application infrastructure and SQL (Structured Query Language) to store, retrieve, and manipulate information stored in them. SQL injection is a code injection technique used to take advantage of coding vulnerabilities and inject SQL queries via an application to bypass authentication, retrieve data from the back-end database, or achieve code execution on the underlying server.
SQLMap Essentials
Easy
Path Sections 11 Sections
Reward: +20
The SQLMap Essentials module will teach you the basics of using SQLMap to discover various types of SQL Injection vulnerabilities, all the way to the advanced enumeration of databases to retrieve all data of interest.
Blind SQL Injection
Hard
Path Sections 16 Sections
Reward: +100
In this module, we cover blind SQL injection attacks and MSSQL-specific attacks.
Advanced SQL Injections
Hard
Path Sections 12 Sections
Reward: +100
This module covers advanced SQL injection techniques with a focus on white-box testing, Java/Spring and PostgreSQL.
File Inclusion
Medium
Path Sections 11 Sections
Reward: +10
File Inclusion is a common web application vulnerability, which can be easily overlooked as part of a web application's functionality.
File Upload Attacks
Medium
Path Sections 11 Sections
Reward: +20
Arbitrary file uploads are among the most critical web vulnerabilities. These flaws enable attackers to upload malicious files, execute arbitrary commands on the back-end server, and even take control over the entire server and all web applications hosted on it and potentially gain access to sensitive data or cause a service disruption.
Command Injections
Medium
Path Sections 12 Sections
Reward: +20
Command injection vulnerabilities can be leveraged to compromise a hosting server and its entire network. This module will teach you how to identify and exploit command injection vulnerabilities and how to use various filter bypassing techniques to avoid security mitigations.
Broken Authentication
Medium
Path Sections 14 Sections
Reward: +20
Authentication is probably the most straightforward and prevalent measure used to secure access to resources, and it's the first line of defense against unauthorized access. Broken authentication is listed as #7 on the 2021 OWASP Top 10 Web Application Security Risks, falling under the broader category of Identification and Authentication failures. A vulnerability or misconfiguration at the authentication stage can impact an application's overall security.
Web Attacks
Medium
Path Sections 18 Sections
Reward: +20
This module covers three common web vulnerabilities, HTTP Verb Tampering, IDOR, and XXE, each of which can have a significant impact on a company's systems. We will cover how to identify, exploit, and prevent each of them through various methods.
HTTPs/TLS Attacks
Medium
Path Sections 15 Sections
Reward: +100
This module covers details on Transport Layer Security (TLS) and how it helps to make HTTP secure with the widely used HTTPS. That includes how TLS works, how TLS sessions are established, common TLS misconfigurations, as well as famous attacks on TLS. We will discuss how to identify, exploit, and prevent TLS attacks.
HTTP Attacks
Hard
Path Sections 18 Sections
Reward: +100
This module covers three HTTP vulnerabilities: CRLF Injection, HTTP Request Smuggling, and HTTP/2 Downgrading. These vulnerabilities can arise on the HTTP level in real-world deployment settings utilizing intermediary systems such as reverse proxies in front of the web server. We will cover how to identify, exploit, and prevent each of these vulnerabilities.
Abusing HTTP Misconfigurations
Hard
Path Sections 20 Sections
Reward: +100
This module covers three common HTTP vulnerabilities: Web Cache Poisoning, Host Header Vulnerabilities, and Session Puzzling or Session Variable Overloading. These vulnerabilities can arise on the HTTP level due to web server misconfigurations, other systems that have to be considered during real-world deployment such as web caches, or coding mistakes in the web application. We will cover how to identify, exploit, and prevent each of these vulnerabilities.
Attacking Common Applications
Medium
Path Sections 33 Sections
Reward: +20
Penetration Testers can come across various applications, such as Content Management Systems, custom web applications, internal portals used by developers and sysadmins, and more. It's common to find the same applications across many different environments. While an application may not be vulnerable in one environment, it may be misconfigured or unpatched in the next. It is important as an assessor to have a firm grasp of enumerating and attacking the common applications discussed in this module. This knowledge will help when encountering other types of applications during assessments.
Web Service & API Attacks
Medium
Path Sections 13 Sections
Reward: +20
Web services and APIs are frequently exposed to provide certain functionalities in a programmatic way between heterogeneous devices and software components. Both web services and APIs can assist in integrating different applications or facilitate separation within a given application. This module covers how to identify the functionality a web service or API offers and exploit any security-related inefficiencies.
Hacking WordPress
Easy
Path Sections 16 Sections
Reward: +20
WordPress is an open-source Content Management System (CMS) that can be used for multiple purposes.
Documentation & Reporting
Easy
Path Sections 8 Sections
Reward: +20
Proper documentation is paramount during any engagement. The end goal of a technical assessment is the report deliverable which will often be presented to a broad audience within the target organization. We must take detailed notes and be very organized in our documentation, which will help us in the event of an incident during the assessment. This will also help ensure that our reports contain enough detail to illustrate the impact of our findings properly.
CREST CCT INF Preparation

CREST CCT INF Preparation

This is a skill path to prepare you for CREST's CCT INF exam. The following CCT INF syllabus areas (IDs) are covered: A1, A2, A3, A4, A5, A8, A9, A10, B1, B2, B4, B5, C1, C2, C3, C4, C6, C7, D1, D2, D5, D9, D10, D13, D14, D15, D18, D19, E1, E2, E3 E6, E7, E8, E9, E11, E13, E14, E15, E16, E17, E18, E19, E20, E25, E26, F1, F2, F3, F4, F5, F6, F7, F8, F9, F10, F11, F12, F13, F15, F16, G1, G2, G3, G4, G5, G6, G7, G8, H1, H2, H3, H4, H5, H6, H7, H8, H9, H10, H11, H12, H13, H14, H15, H16, H17, H19, H20, H21, H23, H24, H25, H26, H27, H28, H29, H30, H31, H32, H33, H34, H35, H36, H37, H38, H40, I1, I2, I3, I4, I6, K1, K2, K3, K4, N1, N2. Take your time to complete all related sections and when you are ready you can book your CREST exam through the following link. https://www.crest-approved.org/certification-careers/crest-certifications/crest-certified-infrastructure-tester/

Hard Path Sections 956 Sections
Required: 11510
Reward: +2430
Path Modules
Introduction to Networking
Fundamental
Path Sections 21 Sections
Reward: +10
As an information security professional, a firm grasp of networking fundamentals and the required components is necessary. Without a strong foundation in networking, it will be tough to progress in any area of information security. Understanding how a network is structured and how the communication between the individual hosts and servers takes place using the various protocols allows us to understand the entire network structure and its network traffic in detail and how different communication standards are handled. This knowledge is essential to create our tools and to interact with the protocols.
Web Requests
Fundamental
Path Sections 8 Sections
Reward: +10
This module introduces the topic of HTTP web requests and how different web applications utilize them to communicate with their backends.
Introduction to Web Applications
Fundamental
Path Sections 17 Sections
Reward: +10
In the Introduction to Web Applications module, you will learn all of the basics of how web applications work and begin to look at them from an information security perspective.
Linux Fundamentals
Fundamental
Path Sections 30 Sections
Reward: +10
This module covers the fundamentals required to work comfortably with the Linux operating system and shell.
Windows Fundamentals
Fundamental
Path Sections 14 Sections
Reward: +10
This module covers the fundamentals required to work comfortably with the Windows operating system.
Introduction to Windows Command Line
Easy
Path Sections 23 Sections
Reward: +10
As administrators and Pentesters, we may not always be able to utilize a graphical user interface for the actions we need to perform. Introduction to Windows Command Line aims to introduce students to the wide range of uses for Command Prompt and PowerShell within a Windows environment. We will cover basic usage of both key executables for administration, useful PowerShell cmdlets and modules, and different ways to leverage these tools to our benefit.
Intro to Network Traffic Analysis
Medium
Path Sections 15 Sections
Reward: +10
Network traffic analysis is used by security teams to monitor network activity and look for anomalies that could indicate security and operational issues. Offensive security practitioners can use network traffic analysis to search for sensitive data such as credentials, hidden applications, reachable network segments, or other potentially sensitive information "on the wire." Network traffic analysis has many uses for attackers and defenders alike.
Brief Intro to Hardware Attacks
mini module tag Mini-Module
Medium
Path Sections 8 Sections
Reward: +10
This mini-module concisely introduces hardware attacks, covering Bluetooth risks and attacks, Cryptanalysis Side-Channel Attacks, and vulnerabilities like Spectre and Meltdown. It delves into both historical and modern Bluetooth hacking techniques, explores the principles of cryptanalysis and different side-channel attacks, and outlines microprocessor design, optimisation strategies and vulnerabilities, such as Spectre and Meltdown.
Penetration Testing Process
Fundamental
Path Sections 15 Sections
Reward: +10
This module teaches the penetration testing process broken down into each stage and discussed in detail. We will cover many aspects of the role of a penetration tester during a penetration test, explained and illustrated with detailed examples. The module also covers pre-engagement steps like the criteria for establishing a contract with a client for a penetration testing engagement.
Network Enumeration with Nmap
Easy
Path Sections 12 Sections
Reward: +10
Nmap is one of the most used networking mapping and discovery tools because of its accurate results and efficiency. The tool is widely used by both offensive and defensive security practitioners. This module covers fundamentals that will be needed to use the Nmap tool for performing effective network enumeration.
Footprinting
Medium
Path Sections 21 Sections
Reward: +20
This module covers techniques for footprinting the most commonly used services in almost all enterprise and business IT infrastructures. Footprinting is an essential phase of any penetration test or security audit to identify and prevent information disclosure. Using this process, we examine the individual services and attempt to obtain as much information from them as possible.
Information Gathering - Web Edition
Easy
Path Sections 19 Sections
Reward: +20
This module equips learners with essential web reconnaissance skills, crucial for ethical hacking and penetration testing. It explores both active and passive techniques, including DNS enumeration, web crawling, analysis of web archives and HTTP headers, and fingerprinting web technologies.
OSINT: Corporate Recon
Hard
Path Sections 23 Sections
Reward: +200
OSINT (Open-source Intelligence) is a crucial stage of the penetration testing process. A thorough examination of publicly available information can increase the chances of finding a vulnerable system, gaining valid credentials through password spraying, or gaining a foothold via social engineering. There is a vast amount of publicly available information from which relevant information needs to be selected.
Vulnerability Assessment
Easy
Path Sections 17 Sections
Reward: +10
This module introduces the concept of Vulnerability Assessments. We will review the differences between vulnerability assessments and penetration tests, how to carry out a vulnerability assessment, how to interpret the assessment results, and how to deliver an effective vulnerability assessment report.
File Transfers
Medium
Path Sections 10 Sections
Reward: +10
During an assessment, it is very common for us to transfer files to and from a target system. This module covers file transfer techniques leveraging tools commonly available across all versions of Windows and Linux systems.
Shells & Payloads
Medium
Path Sections 17 Sections
Reward: +10
Gain the knowledge and skills to identify and use shells & payloads to establish a foothold on vulnerable Windows & Linux systems. This module utilizes a fictitious scenario where the learner will place themselves in the perspective of a sysadmin trying out for a position on CAT5 Security's network penetration testing team.
Using the Metasploit Framework
Easy
Path Sections 15 Sections
Reward: +10
The Metasploit Framework is an open-source set of tools used for network enumeration, attacks, testing security vulnerabilities, evading detection, performing privilege escalation attacks, and performing post-exploitation.
Password Attacks
Medium
Path Sections 22 Sections
Reward: +10
Passwords are still the primary method of authentication in corporate networks. If strong password policies are not in place, users will often opt for weak, easy-to-remember passwords that can often be cracked offline and used to further our access. We will encounter passwords in many forms during our assessments. We must understand the various ways they are stored, how they can be retrieved, methods to crack weak passwords, ways to use hashes that cannot be cracked, and hunting for weak/default password usage.
Attacking Common Services
Medium
Path Sections 19 Sections
Reward: +20
Organizations regularly use a standard set of services for different purposes. It is vital to conduct penetration testing activities on each service internally and externally to ensure that they are not introducing security threats. This module will cover how to enumerate each service and test it against known vulnerabilities and exploits with a standard set of tools.
Cracking Passwords with Hashcat
Medium
Path Sections 14 Sections
Reward: +20
This module covers the fundamentals of password cracking using the Hashcat tool.
Introduction to Active Directory
Fundamental
Path Sections 16 Sections
Reward: +10
Active Directory (AD) is present in the majority of corporate environments. Due to its many features and complexity, it presents a vast attack surface. To be successful as penetration testers and information security professionals, we must have a firm understanding of Active Directory fundamentals, AD structures, functionality, common AD flaws, misconfigurations, and defensive measures.
Active Directory LDAP
Medium
Path Sections 12 Sections
Reward: +100
This module provides an overview of Active Directory (AD), introduces core AD enumeration concepts, and covers enumeration with built-in tools.
Active Directory PowerView
Medium
Path Sections 9 Sections
Reward: +100
This module covers AD enumeration focusing on the PowerView and SharpView tools. We will cover various techniques for enumerating key AD objects that will inform our attacks in later modules.
Active Directory BloodHound
Medium
Path Sections 14 Sections
Reward: +100
This module covers AD enumeration focusing on the BloodHound tool. We will cover various techniques for enumerating key AD objects that will inform our attacks in later modules.
Pivoting, Tunneling, and Port Forwarding
Medium
Path Sections 18 Sections
Reward: +20
Once a foothold is gained during an assessment, it may be in scope to move laterally and vertically within a target network. Using one compromised machine to access another is called pivoting and allows us to access networks and resources that are not directly accessible to us through the compromised host. Port forwarding accepts the traffic on a given IP address and port and redirects it to a different IP address and port combination. Tunneling is a technique that allows us to encapsulate traffic within another protocol so that it looks like a benign traffic stream.
Active Directory Enumeration & Attacks
Medium
Path Sections 36 Sections
Reward: +20
Active Directory (AD) is the leading enterprise domain management suite, providing identity and access management, centralized domain administration, authentication, and much more. Due to the many features and complexity of AD, it presents a large attack surface that is difficult to secure properly. To be successful as infosec professionals, we must understand AD architectures and how to secure our enterprise environments. As Penetration testers, having a firm grasp of what tools, techniques, and procedures are available to us for enumerating and attacking AD environments and commonly seen AD misconfigurations is a must.
Kerberos Attacks
Hard
Path Sections 23 Sections
Reward: +100
Kerberos is an authentication protocol that allows users to authenticate and access services on a potentially insecure network. Due to its prevalence throughout an Active Directory environment, it presents us with a significant attack surface when assessing internal networks. This module will explain how Kerberos works thoroughly and examines several scenarios to practice the most common attacks against it from multiple perspectives.
DACL Attacks I
mini module tag Mini-Module
Hard
Path Sections 7 Sections
Reward: +100
Discretionary Access Control Lists (DACLs), found within security descriptors, are a fundamental component of the security model of Windows and Active Directory, defining and enforcing access to the various system resources. This mini-module will cover enumerating and attacking common DACL misconfigurations, allowing us to escalate our privileges horizontally and vertically and move laterally across an Active Directory network.
Using CrackMapExec
Medium
Path Sections 27 Sections
Reward: +100
Active Directory presents a vast attack surface and often requires us to use many different tools during an assessment. The CrackMapExec tool, known as a "Swiss Army Knife" for testing networks, facilitates enumeration, attacks, and post-exploitation that can be leveraged against most any domain using multiple network protocols. It is a versatile and highly customizable tool that should be in any penetration tester's toolbox.
Linux Privilege Escalation
Easy
Path Sections 28 Sections
Reward: +20
Privilege escalation is a crucial phase during any security assessment. During this phase, we attempt to gain access to additional users, hosts, and resources to move closer to the assessment's overall goal. There are many ways to escalate privileges. This module aims to cover the most common methods emphasizing real-world misconfigurations and flaws that we may encounter in a client environment. The techniques covered in this module are not an exhaustive list of all possibilities and aim to avoid extreme "edge-case" tactics that may be seen in a Capture the Flag (CTF) exercise.
Windows Privilege Escalation
Medium
Path Sections 33 Sections
Reward: +20
After gaining a foothold, elevating our privileges will provide more options for persistence and may reveal information stored locally that can further our access in the environment. Enumeration is the key to privilege escalation. When you gain initial shell access to the host, it is important to gain situational awareness and uncover details relating to the OS version, patch level, any installed software, our current privileges, group memberships, and more. Windows presents an enormous attack surface and, being that most companies run Windows hosts in some way, we will more often than not find ourselves gaining access to Windows machines during our assessments. This covers common methods while emphasizing real-world misconfigurations and flaws that we may encounter during an assessment. There are many additional "edge-case" possibilities not covered in this module. We will cover both modern and legacy Windows Server and Desktop versions that may be present in a client environment.
Stack-Based Buffer Overflows on Linux x86
Medium
Path Sections 13 Sections
Reward: +10
Buffer overflows are common vulnerabilities in software applications that can be exploited to achieve remote code execution (RCE) or perform a Denial-of-Service (DoS) attack. These vulnerabilities are caused by insecure coding, resulting in an attacker being able to overrun a program's buffer and overwrite adjacent memory locations, changing the program's execution path and resulting in unintended actions.
Stack-Based Buffer Overflows on Windows x86
Medium
Path Sections 11 Sections
Reward: +10
This module is your first step into Windows Binary Exploitation, and it will teach you how to exploit local and remote buffer overflow vulnerabilities on Windows machines.
Using Web Proxies
Easy
Path Sections 15 Sections
Reward: +20
Web application penetration testing frameworks are an essential part of any web penetration test. This module will teach you two of the best frameworks: Burp Suite and OWASP ZAP.
Attacking Web Applications with Ffuf
Easy
Path Sections 13 Sections
Reward: +10
This module covers the fundamental enumeration skills of web fuzzing and directory brute forcing using the Ffuf tool. The techniques learned in this module will help us in locating hidden pages, directories, and parameters when targeting web applications.
Login Brute Forcing
Easy
Path Sections 13 Sections
Reward: +20
The module contains an exploration of brute-forcing techniques, including the use of tools like Hydra and Medusa, and the importance of strong password practices. It covers various attack scenarios, such as targeting SSH, FTP, and web login forms.
Cross-Site Scripting (XSS)
Easy
Path Sections 10 Sections
Reward: +20
Cross-Site Scripting (XSS) vulnerabilities are among the most common web application vulnerabilities. An XSS vulnerability may allow an attacker to execute arbitrary JavaScript code within the target's browser and result in complete web application compromise if chained together with other vulnerabilities. This module will teach you how to identify XSS vulnerabilities and exploit them.
Session Security
Medium
Path Sections 14 Sections
Reward: +20
Maintaining and keeping track of a user's session is an integral part of web applications. It is an area that requires extensive testing to ensure it is set up robustly and securely. This module covers the most common attacks and vulnerabilities that can affect web application sessions, such as Session Hijacking, Session Fixation, Cross-Site Request Forgery, Cross-Site Scripting, and Open Redirects.
SQL Injection Fundamentals
Medium
Path Sections 17 Sections
Reward: +10
Databases are an important part of web application infrastructure and SQL (Structured Query Language) to store, retrieve, and manipulate information stored in them. SQL injection is a code injection technique used to take advantage of coding vulnerabilities and inject SQL queries via an application to bypass authentication, retrieve data from the back-end database, or achieve code execution on the underlying server.
SQLMap Essentials
Easy
Path Sections 11 Sections
Reward: +20
The SQLMap Essentials module will teach you the basics of using SQLMap to discover various types of SQL Injection vulnerabilities, all the way to the advanced enumeration of databases to retrieve all data of interest.
Blind SQL Injection
Hard
Path Sections 16 Sections
Reward: +100
In this module, we cover blind SQL injection attacks and MSSQL-specific attacks.
Advanced SQL Injections
Hard
Path Sections 12 Sections
Reward: +100
This module covers advanced SQL injection techniques with a focus on white-box testing, Java/Spring and PostgreSQL.
Introduction to NoSQL Injection
Medium
Path Sections 12 Sections
Reward: +100
In this module, we will look at exploiting NoSQL injection vulnerabilities, specifically MongoDB, with examples in Python, PHP, and Node.JS.
File Inclusion
Medium
Path Sections 11 Sections
Reward: +10
File Inclusion is a common web application vulnerability, which can be easily overlooked as part of a web application's functionality.
File Upload Attacks
Medium
Path Sections 11 Sections
Reward: +20
Arbitrary file uploads are among the most critical web vulnerabilities. These flaws enable attackers to upload malicious files, execute arbitrary commands on the back-end server, and even take control over the entire server and all web applications hosted on it and potentially gain access to sensitive data or cause a service disruption.
Command Injections
Medium
Path Sections 12 Sections
Reward: +20
Command injection vulnerabilities can be leveraged to compromise a hosting server and its entire network. This module will teach you how to identify and exploit command injection vulnerabilities and how to use various filter bypassing techniques to avoid security mitigations.
Broken Authentication
Medium
Path Sections 14 Sections
Reward: +20
Authentication is probably the most straightforward and prevalent measure used to secure access to resources, and it's the first line of defense against unauthorized access. Broken authentication is listed as #7 on the 2021 OWASP Top 10 Web Application Security Risks, falling under the broader category of Identification and Authentication failures. A vulnerability or misconfiguration at the authentication stage can impact an application's overall security.
Web Attacks
Medium
Path Sections 18 Sections
Reward: +20
This module covers three common web vulnerabilities, HTTP Verb Tampering, IDOR, and XXE, each of which can have a significant impact on a company's systems. We will cover how to identify, exploit, and prevent each of them through various methods.
HTTPs/TLS Attacks
Medium
Path Sections 15 Sections
Reward: +100
This module covers details on Transport Layer Security (TLS) and how it helps to make HTTP secure with the widely used HTTPS. That includes how TLS works, how TLS sessions are established, common TLS misconfigurations, as well as famous attacks on TLS. We will discuss how to identify, exploit, and prevent TLS attacks.
HTTP Attacks
Hard
Path Sections 18 Sections
Reward: +100
This module covers three HTTP vulnerabilities: CRLF Injection, HTTP Request Smuggling, and HTTP/2 Downgrading. These vulnerabilities can arise on the HTTP level in real-world deployment settings utilizing intermediary systems such as reverse proxies in front of the web server. We will cover how to identify, exploit, and prevent each of these vulnerabilities.
Injection Attacks
Medium
Path Sections 15 Sections
Reward: +100
This module covers three injection attacks: XPath injection, LDAP injection, and HTML injection in PDF generation libraries. While XPath and LDAP injection vulnerabilities can lead to authentication bypasses and data exfiltration, HTML injection in PDF generation libraries can lead to Server-Side Request Forgery (SSRF), Local File Inclusion (LFI), and other common web vulnerabilities. We will cover how to identify, exploit, and prevent each of these injection attacks.
Abusing HTTP Misconfigurations
Hard
Path Sections 20 Sections
Reward: +100
This module covers three common HTTP vulnerabilities: Web Cache Poisoning, Host Header Vulnerabilities, and Session Puzzling or Session Variable Overloading. These vulnerabilities can arise on the HTTP level due to web server misconfigurations, other systems that have to be considered during real-world deployment such as web caches, or coding mistakes in the web application. We will cover how to identify, exploit, and prevent each of these vulnerabilities.
Attacking Common Applications
Medium
Path Sections 33 Sections
Reward: +20
Penetration Testers can come across various applications, such as Content Management Systems, custom web applications, internal portals used by developers and sysadmins, and more. It's common to find the same applications across many different environments. While an application may not be vulnerable in one environment, it may be misconfigured or unpatched in the next. It is important as an assessor to have a firm grasp of enumerating and attacking the common applications discussed in this module. This knowledge will help when encountering other types of applications during assessments.
Web Service & API Attacks
Medium
Path Sections 13 Sections
Reward: +20
Web services and APIs are frequently exposed to provide certain functionalities in a programmatic way between heterogeneous devices and software components. Both web services and APIs can assist in integrating different applications or facilitate separation within a given application. This module covers how to identify the functionality a web service or API offers and exploit any security-related inefficiencies.
Hacking WordPress
Easy
Path Sections 16 Sections
Reward: +20
WordPress is an open-source Content Management System (CMS) that can be used for multiple purposes.
Documentation & Reporting
Easy
Path Sections 8 Sections
Reward: +20
Proper documentation is paramount during any engagement. The end goal of a technical assessment is the report deliverable which will often be presented to a broad audience within the target organization. We must take detailed notes and be very organized in our documentation, which will help us in the event of an incident during the assessment. This will also help ensure that our reports contain enough detail to illustrate the impact of our findings properly.
Secure Coding 101: JavaScript
Hard
Path Sections 17 Sections
Reward: +200
Learn how to improve your JavaScript code's security through Code Review, Static/Dynamic Analysis, Vulnerability Identification, and Patching.
Whitebox Attacks
Hard
Path Sections 15 Sections
Reward: +100
This module explores several web vulnerabilities from a whitebox approach: Prototype Pollution, Timing Attacks & Race Conditions, and those arising from Type Juggling. We will discuss how to identify, exploit, and prevent each vulnerability.
Senior Web Penetration Tester

Senior Web Penetration Tester

The Senior Web Penetration Tester Job Role Path is designed for individuals who aim to develop skills in identifying advanced and hard-to-find web vulnerabilities using both black box and white box techniques. This path encompasses advanced-level training in web security, web penetration testing, and secure coding concepts. It also provides a deep understanding of the application debugging, source code review, and custom exploit development aspects of web security. Equipped with the necessary theoretical background, multiple practical exercises, and a proven methodology for web vulnerability identification, students will eventually be capable of performing professional security assessments against modern and highly secure web applications, as well as effectively reporting vulnerabilities found in code or arising from logical errors.

Hard Path Sections 245 Sections
Required: 7500
Reward: +1500
Path Modules
Injection Attacks
Medium
Path Sections 15 Sections
Reward: +100
This module covers three injection attacks: XPath injection, LDAP injection, and HTML injection in PDF generation libraries. While XPath and LDAP injection vulnerabilities can lead to authentication bypasses and data exfiltration, HTML injection in PDF generation libraries can lead to Server-Side Request Forgery (SSRF), Local File Inclusion (LFI), and other common web vulnerabilities. We will cover how to identify, exploit, and prevent each of these injection attacks.
Introduction to NoSQL Injection
Medium
Path Sections 12 Sections
Reward: +100
In this module, we will look at exploiting NoSQL injection vulnerabilities, specifically MongoDB, with examples in Python, PHP, and Node.JS.
Attacking Authentication Mechanisms
Medium
Path Sections 20 Sections
Reward: +100
Authentication plays an essential role in almost every web application. If a vulnerability arises in the application's authentication mechanism, it could result in unauthorized access, data loss, or potentially even remote code execution, depending on the application's functionality. This module will provide an overview of various access control methods, such as JWT, OAuth, and SAML, and potential attacks against each.
Advanced XSS and CSRF Exploitation
Medium
Path Sections 17 Sections
Reward: +100
Modern web browsers and applications utilize a variety of security measures to protect against CSRF and XSS vulnerabilities, rendering their exploitation more difficult. This module focuses on exploiting advanced CSRF and XSS vulnerabilities, identifying and bypassing weak and wrongly implemented defensive mechanisms.
HTTPs/TLS Attacks
Medium
Path Sections 15 Sections
Reward: +100
This module covers details on Transport Layer Security (TLS) and how it helps to make HTTP secure with the widely used HTTPS. That includes how TLS works, how TLS sessions are established, common TLS misconfigurations, as well as famous attacks on TLS. We will discuss how to identify, exploit, and prevent TLS attacks.
Abusing HTTP Misconfigurations
Hard
Path Sections 20 Sections
Reward: +100
This module covers three common HTTP vulnerabilities: Web Cache Poisoning, Host Header Vulnerabilities, and Session Puzzling or Session Variable Overloading. These vulnerabilities can arise on the HTTP level due to web server misconfigurations, other systems that have to be considered during real-world deployment such as web caches, or coding mistakes in the web application. We will cover how to identify, exploit, and prevent each of these vulnerabilities.
HTTP Attacks
Hard
Path Sections 18 Sections
Reward: +100
This module covers three HTTP vulnerabilities: CRLF Injection, HTTP Request Smuggling, and HTTP/2 Downgrading. These vulnerabilities can arise on the HTTP level in real-world deployment settings utilizing intermediary systems such as reverse proxies in front of the web server. We will cover how to identify, exploit, and prevent each of these vulnerabilities.
Blind SQL Injection
Hard
Path Sections 16 Sections
Reward: +100
In this module, we cover blind SQL injection attacks and MSSQL-specific attacks.
Intro to Whitebox Pentesting
Hard
Path Sections 18 Sections
Reward: +100
Whitebox penetration testing enables thorough testing to identify various hard-to-find vulnerabilities. This module covers the process of whitebox pentesting and follows that with a practical demo by exploiting an advanced code injection vulnerability.
Modern Web Exploitation Techniques
Hard
Path Sections 18 Sections
Reward: +100
This module covers advanced web concepts and exploitation techniques, including performing DNS Rebinding to bypass faulty SSRF filters and the Same-Origin Policy, identifying and exploiting Second-Order vulnerabilities, and conducting common web attacks via WebSocket connections.
Introduction to Deserialization Attacks
Hard
Path Sections 15 Sections
Reward: +100
In this module, we will explore deserialization attacks with specific examples in Python and PHP.
Whitebox Attacks
Hard
Path Sections 15 Sections
Reward: +100
This module explores several web vulnerabilities from a whitebox approach: Prototype Pollution, Timing Attacks & Race Conditions, and those arising from Type Juggling. We will discuss how to identify, exploit, and prevent each vulnerability.
Advanced SQL Injections
Hard
Path Sections 12 Sections
Reward: +100
This module covers advanced SQL injection techniques with a focus on white-box testing, Java/Spring and PostgreSQL.
Advanced Deserialization Attacks
Hard
Path Sections 13 Sections
Reward: +100
This module focuses on developing custom exploits for .NET deserialization vulnerabilities from a whitebox perspective.
Parameter Logic Bugs
Hard
Path Sections 21 Sections
Reward: +100
This 'secure coding' module teaches how to identify logic bugs through code review and analysis, and covers three types of logic bugs caused by user input manipulation.