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HTTPs/TLS Attacks

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.

4.54

Created by vautia

Medium Offensive

Summary

Transport Layer Security (TLS) is the standard protocol that is responsible for providing secure communication over the internet, including securing the unencrypted HTTP protocol to form HTTPS. As such it is used to secure a wide variety of services and applications. Therefore, vulnerabilities and misconfigurations in TLS can have catastrophic consequences. This module covers basics about the inner workings of TLS, as well as famous TLS attacks and common misconfigurations.

In more detail, this module covers the following:

  • Introduction to HTTPS/TLS
    • What is TLS and how does it relate to HTTPS?
    • Theoretical background knowledge about public key infrastructure (PKI)
    • Overview of the TLS 1.2 handshake and how TLS sessions are established
    • Overview of the TLS 1.3 handshake
  • Padding Oracle Attacks
    • What are padding oracles?
    • How to identify padding oracles
    • How to exploit padding oracles
    • What is a Bleichenbacher attack?
  • TLS Compression
    • Introduction to TLS compression
    • Attacks on TLS compression
  • Heartbleed Bug
    • What is the Heartbleed bug?
    • How to identify & exploit the Heartbleed bug
  • Misc Attacks
    • What is SSL Stripping?
    • How can we prevent SSL Stripping?
    • Overview of cryptographic attacks against TLS
    • What are Downgrade attacks?
  • TLS Best Practices
    • What are best practices for TLS servers?
    • How can we test the TLS configuration of TLS servers?

CREST CPSA/CRT-related Sections:

  • All sections

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

Introduction to HTTPS/TLS

The Hypertext Transfer Protocol (HTTP) is an application layer protocol used to access resources on the internet. Since HTTP transmits data in plaintext, it cannot provide confidentiality, integrity, or authenticity of the transmitted data. To overcome these shortcomings of HTTP, the Hypertext Transfer Protocol Secure (HTTPS), also called HTTP over TLS was created. The Transport Layer Security (TLS) protocol and its predecessor, the Secure Sockets Layer (SSL) protocol, are cryptographic protocols that provide secure communication over the internet by encrypting traffic.

Encryption can generally be applied at different levels. These include encryption-at-rest, encryption-in-transit, and end-to-end encryption. Encryption-at-rest means that data is stored in an encrypted form to prevent unauthorized access. An example would be hard drive encryption. When encryption-in-transit is applied, data that is transmitted is encrypted before transmission and decrypted after reception to prevent unauthorized access during the transmission. This module focuses on encryption-in-transit since TLS applies encryption-in-transit. Lastly, end-to-end encryption encrypts data from the true sender to the final recipient such that no other party can access the data.

To illustrate the difference to encryption-in-transit, consider Alice who wants to send an email to Bob. If they use end-to-end encryption, Alice encrypts the e-mail and sends it to Bob who decrypts it to access the e-mail. No intermediary servers that the encrypted e-mail is routed over can access it. When TLS and thus encryption-in-transit is used, Alice encrypts the e-mail and sends it to her mail server, which decrypts it, and re-encrypts it to forward it to the next server, and so on until the final server sends it to Bob. This protects the email from any unauthorized access during transit but all intermediary servers can access the e-mail in plaintext, while only Alice and Bob can access the e-mail if end-to-end encryption is used.

The main purpose of this module is to provide insights into web cryptography protocols, how they work, and what vulnerabilities can arise when using them. Generally speaking, finding vulnerabilities in protocols is more challenging compared to finding vulnerabilities in individual web applications. That is because protocols such as HTTPS and TLS have been designed with security in mind and revised multiple times to tackle potential security issues. However, if there are security issues in protocols, the impact is generally much higher as well since a huge number of services are affected. Oftentimes, security issues on HTTPS or TLS are not specification flaws but implementation flaws. That means that specific implementations of the protocol do not implement the protocol correctly or deviate slightly which can create security issues.

TLS Overview and Version History

What is TLS?

TLS and before it SSL are widely used to secure communication on the internet, including email, file transfer, and web browsing. TLS was developed to address the weaknesses in SSL and has undergone several revisions over the years, each of which has introduced new features and improvements to the protocol. Today, TLS is the standard protocol for secure communication on the internet.

In the network protocol stack, TLS sits between TCP and the application layer, which can be any application layer protocol such as HTTP, SMTP, or FTP. TLS is transparent for the application layer protocol, meaning the application layer protocol does not need to know if TLS is implemented or not. In particular, TLS takes care of all cryptographic operations, the application layer protocol can operate the same regardless of whether TLS is used or not.

Version History

SSL was first developed by Netscape in the mid-1990s as a way to secure communication over the internet. It quickly became the standard protocol for secure communication and was widely adopted by web browsers and servers. There are three major versions of SSL:

  • SSL 1.0: This was the initial version of SSL. It was never released to the public due to serious security flaws.
  • SSL 2.0: This was the first SSL version that became widely used. It was released in 1995. However, it suffered from multiple serious specification flaws that made it impractical to use in some cases and susceptible to cryptographic attacks.
  • SSL 3.0: This was the last version of SSL. It is a full redesign of the 2.0 version that fixed the specification flaws. However, from today's perspective, it relies on deprecated cryptographic algorithms and is vulnerable to a variety of attacks.

In response to weaknesses in SSL, the TLS protocol was developed to replace it. TLS was designed to address the vulnerabilities in SSL and to provide stronger encryption and authentication for secure communication. Like SSL, TLS has undergone several revisions, each of which has introduced new features and improvements to the protocol. Some of the key versions of TLS include:

  • TLS 1.0: This was the first version of TLS and was released in 1999. It was based on SSL 3.0 and included many of the same features as SSL, but with additional security enhancements.
  • TLS 1.1: This version of TLS was released in 2006 and introduced several important improvements to the protocol, including support for new cryptographic algorithms and protection against attacks such as man-in-the-middle attacks (aka On-Path Attacks).
  • TLS 1.2: This version of TLS was released in 2008 and introduced further security enhancements, including support for stronger cryptographic algorithms and better protection against attacks. It also introduced new features such as the ability to negotiate the use of compression during the handshake process.
  • TLS 1.3: This is the latest version of TLS, released in 2018. It includes significant improvements to the protocol, including faster performance, stronger encryption, and better protection against attacks. It also includes a simplified handshake process and the ability to negotiate the use of encryption during the handshake process.

In this module, we will discuss attacks that broke certain SSL/TLS protocol versions completely, including SSL 2.0 and SSL 3.0.

What is HTTPS?

Now that we have a basic understanding of what TLS is, let's discuss how TLS relates to HTTPS. HTTPS works the same as HTTP, however in HTTPS, TLS is contained in the protocol stack. That means HTTPS traffic is encrypted and integrity protected thus preventing attackers from eavesdropping on or manipulating data. While HTTP uses the protocol scheme http:// and targets port 80 by default, HTTPS uses https:// and targets port 443. Although there are different HTTP versions, HTTPS only means that the HTTP traffic is encapsulated in TLS. Thus, there are no dedicated HTTPS versions.

Introduction to TLS Attacks

The Transport Layer Security (TLS) protocol and its predecessor, the Secure Sockets Layer (SSL) protocol, are cryptographic protocols that provide secure communication over the internet. TLS protects the confidentiality, integrity, and authenticity of transmitted data. To provide these security services, TLS utilizes a combination of cryptographic algorithms such as symmetric encryption, asymmetric encryption, and Message Authentication Codes (MACs).

In this module, we will take a closer look at TLS to gain a broad understanding of how TLS works and what things to look out for when testing TLS configurations. We will discuss common TLS security vulnerabilities to understand what misconfiguration or bugs caused them. Finally, we will discuss how to detect, exploit, and prevent each of these attacks as well as common misconfigurations regarding TLS servers.

Padding Oracle Attacks

The first type of TLS attacks discussed in this module are Padding Oracle attacks. Padding oracle attacks exploit vulnerable servers that leak information about the correctness of the padding after decrypting a received ciphertext. These attacks can enable an attacker to fully decrypt a ciphertext without knowledge of the encryption key. Examples of Padding Oracle attacks on TLS are the POODLE, DROWN, and Bleichenbacher attacks.

Compression Attacks

The second type of TLS attacks discussed in this module are compression attacks. Compression can be applied at the HTTP level or TLS level to increase the performance of data transmission. However, incorrectly configured servers can be exploited, resulting in the leakage of encrypted information such as session cookies or CSRF tokens. Examples of compression-based attacks on TLS are the CRIME and BREACH attacks.

Misc Attacks & Misconfigurations

The last type of TLS attacks discussed in this module are various other attacks that exploit misconfigurations or bugs. A famous example is the Heartbleed bug that exploits a missing length validation in the OpenSSL library, which can lead to a complete server takeover via private key leakage. We will also discuss different TLS misconfigurations that can weaken TLS security by using insecure cryptographic primitives.

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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 CPSA/CRT Preparation

CREST CPSA/CRT Preparation

This is a skill path to prepare you for CREST's CPSA and CRT exams. The following CPSA/CRT 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, H8, H9, H10, H11, H12, H13, I1, I2, I3, I6, 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 links. CREST CPSA: https://www.crest-approved.org/certification-careers/crest-certifications/crest-practitioner-security-analyst/. CREST CRT: https://www.crest-approved.org/certification-careers/crest-certifications/crest-registered-penetration-tester/.

Medium Path Sections 839 Sections
Required: 6800
Reward: +1480
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.
Windows Event Logs & Finding Evil
mini module tag Mini-Module
Medium
Path Sections 6 Sections
Reward: +20
This module covers the exploration of Windows Event Logs and their significance in uncovering suspicious activities. Throughout the course, we delve into the anatomy of Windows Event Logs and highlight the logs that hold the most valuable information for investigations. The module also focuses on utilizing Sysmon and Event Logs for detecting and analyzing malicious behavior. Additionally, we delve into Event Tracing for Windows (ETW), explaining its architecture and components, and provide ETW-based detection examples. To streamline the analysis process, we introduce the powerful Get-WinEvent cmdlet.
Introduction to Malware Analysis
Hard
Path Sections 9 Sections
Reward: +20
This module offers an exploration of malware analysis, specifically targeting Windows-based threats. The module covers Static Analysis utilizing Linux and Windows tools, Malware Unpacking, Dynamic Analysis (including malware traffic analysis), Reverse Engineering for Code Analysis, and Debugging using x64dbg. Real-world malware examples such as WannaCry, DoomJuice, Brbbot, Dharma, and Meterpreter are analyzed to provide practical experience.
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.
Intermediate Network Traffic Analysis
Easy
Path Sections 18 Sections
Reward: +20
Through network traffic analysis, this module sharpens skills in detecting link layer attacks such as ARP anomalies and rogue access points, identifying network abnormalities like IP spoofing and TCP handshake irregularities, and uncovering application layer threats from web-based vulnerabilities to peculiar DNS activities.
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 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 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.
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.
NTLM Relay Attacks
Hard
Path Sections 10 Sections
Reward: +100
The NTLM authentication protocol is commonly used within Windows-based networks to facilitate authentication between clients and servers. However, NTLM's inherent weaknesses make it susceptible to Adversary-in-the-Middle attacks, providing a significant attack vector. This module focuses on the various NTLM relay attacks that attackers use to compromise Active Directory networks.
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.
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.
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.
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.
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.
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.
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.
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.
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.