Windows Privilege Escalation

Windows Privilege Escalation  Medium

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.

Created by mrb3n

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Summary

This module covers a wide variety of techniques that can be utilized to escalate privileges on Windows systems. Privilege escalation is an essential part of a penetration test or red team assessment. Having a deep understanding of the Windows operating system, strong enumeration skills, using built-in tools and features, and knowledge of many local privilege escalation techniques can make or break an assessment and set us apart from others in the field.

In this module, we will cover:

  • Useful tools
  • Situational awareness and initial enumeration of Windows systems
  • Leveraging user and group inherited privileges
  • Attacks against the Windows operating system such as kernel exploits and weak permissions
  • Recent attacks
  • Credential theft techniques
  • Attacking users
  • Dealing with legacy Server and Desktop systems
  • Windows hardening best practices

This module is broken down 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.

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 target host provided in the interactive sections or your virtual machine.

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.

The module is classified as "Medium" and assumes a working knowledge of the Windows command line and operating system fundamentals and a fundamental understanding of information security principles.

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

  • Introduction to Networking
  • Windows Fundamentals

Sections

  • Introduction to Windows Privilege Escalation
  • Useful Tools
  • Situational Awareness
  • Initial Enumeration
  • Communication with Processes
  • Windows Privileges Overview
  • SeImpersonate and SeAssignPrimaryToken
  • SeDebugPrivilege
  • SeTakeOwnershipPrivilege
  • Windows Built-in Groups
  • Event Log Readers
  • DnsAdmins
  • Hyper-V Administrators
  • Print Operators
  • Server Operators
  • User Account Control
  • Weak Permissions
  • Kernel Exploits
  • Vulnerable Services
  • Credential Hunting
  • Other Files
  • Further Credential Theft
  • Interacting with Users
  • Miscellaneous Techniques
  • Legacy Operating Systems
  • Windows Server
  • Windows Desktop Versions
  • Windows Hardening
  • Windows Privilege Escalation Skills Assessment - Part I
  • Windows Privilege Escalation Skills Assessment - Part II

Relevant Paths

This module progresses you towards the following Paths

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Local Privilege Escalation

Medium 45 Sections

Cubes Required: 1000

Privilege escalation is a vital phase of the penetration testing process, one we may revisit multiple times during an engagement. During our assessments, we will encounter a large variety of operating systems and applications. Most often, if we can exploit a vulnerability and gain a foothold on a host, it will be running some version of Windows or Linux. Both present a large attack surface with many tactics and techniques available to us for escalating privileges. This path teaches the core concepts of local privilege escalation necessary for being successful against Windows and Linux systems. The path covers manual enumeration and exploitation and the use of tools to aid in the process.

 Linux Privilege Escalation

Easy 15 Sections

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 30 Sections

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.

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Junior Penetration Tester

Medium 246 Sections

Cubes Required: 3150

The Junior Penetration Tester Job Role Path is for newcomers to information security who aspire to become professional penetration testers. This path covers core security assessment concepts and provides a deep understanding of the specialized tools, attack tactics, and methodology used during penetration testing. Armed with the necessary theoretical background and multiple practical exercises, students will go through all penetration testing stages, from reconnaissance and enumeration to documentation and reporting. Upon completing our first job role path, you will have obtained the practical skills and mindset necessary to perform professional security assessments against enterprise-level infrastructure at a basic to intermediate level.

 The Penetration Testing Process

Easy 1 Sections

This module teaches the entire penetration testing process and its stages, which will be discussed in detail as this will be an essential part of our work. We cover many aspects of the role of a penetration tester in 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.

 Getting Started

Fundamental 23 Sections

This module covers the fundamentals of penetration testing and an introduction to Hack The Box.

 Introduction to Metasploit Framework

Easy 1 Sections

The Metasploit Framework is an open-source set of tools used for network enumeration, identifying and testing security vulnerabilities, payload creation, exploitation, and post-exploitation activities. Since Metasploit is open-source, penetration testers and even blue team members can use it to probe networks and applications for flaws and vulnerabilities through ready-made code and custom code.

 Shells and Payloads

Medium 1 Sections

Understanding the correct type of payload to use or the functions of different shells can be the difference between getting discovered during a penetration test or moving on undetected. This module will cover many different methods of establishing a shell on a host and creating payloads to match your victim's applications and architecture.

 Reconnaissance

Easy 1 Sections

This module covers techniques for footprinting the most commonly used services in enterprise and business IT infrastructures. Footprinting is an essential part of any penetration test or security audit to identify and prevent information disclosure. It examines the individual services and tries to obtain as much information from them as possible.

 Network Enumeration with Nmap

Easy 12 Sections

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.

 Vulnerability Assessment

Easy 1 Sections

This module contains an introduction to Vulnerability Assessment and the related frameworks. Students will review the differences between vulnerability assessments and penetration tests, how to carry out a vulnerability assessment, how to interpret vulnerability assessment results, and how to deliver an effective vulnerability assessment report.

 Attacking Common Services

Medium 9 Sections

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.

 AD Enumeration and Attacks

Medium 1 Sections

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 in general, we must have a firm grasp of tactics and techniques for enumerating and attacking common AD flaws and misconfigurations.

 Using Web Proxies

Easy 15 Sections

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.

 Login Brute Forcing

Easy 11 Sections

Learn how to brute force logins for various types of services and create custom wordlists based on your target.

 Attacking Web Applications with Ffuf

Easy 13 Sections

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.

 Cross-Site Scripting (XSS)

Easy 10 Sections

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.

 Web Attacks

Medium 18 Sections

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 22 Sections

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.

 File Inclusion / Directory Traversal

Medium 7 Sections

File Inclusion is a common web application vulnerability, which can be easily overlooked as part of a web application's functionality.

 SQL Injection Fundamentals

Medium 17 Sections

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 11 Sections

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.

 Command Injections

Medium 12 Sections

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.

 Unrestricted File Upload

Medium 1 Sections

Unrestricted file upload vulnerabilities are among the most critical web vulnerabilities, as they can enable attackers to upload malicious files and execute arbitrary commands on the back-end server. This module will discuss the basics of identifying and exploiting unrestricted file upload vulnerabilities and how to evade basic security restrictions in place to achieve arbitrary file uploading.

 Linux Privilege Escalation

Easy 15 Sections

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 30 Sections

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.

 File Transfers

Medium 8 Sections

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.

 Pillaging

Medium 1 Sections

Pillaging is the process of obtaining information from a compromised system. It can be personal information, corporate blueprints, credit card details or passwords, and other credentials. These may help in gaining further access to the network or in completing goals defined in the pre-engagement process of penetration testing. This data may be stored in a wide range of different applications, services, and device types, which may require specific tools to obtain them.

 Password Attacks

Medium 1 Sections

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 "replay" passwords that cannot be cracked, and hunting for weak/default password usage.

 Pivoting, Tunneling & Port Forwarding

Medium 1 Sections

Once a foothold is gained during assessments, 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.

 AD Lateral Movement Fundamentals

Medium 1 Sections

Once an initial foothold is gained during Active Directory penetration testing assessments, we usually look for ways to move laterally within a target network. Many techniques can be used for lateral movement, including credential theft and reuse, using protocols for system management and administration, remote exploits, password guessing attacks, and more. This module showcases various Active Directory lateral movement techniques that can be used depending on the technologies present within the host and network.

 Documentation & Reporting

Easy 1 Sections

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 help ensure that our reports contain enough detail to illustrate the impact of our findings properly.

 Attacking Enterprise Networks

Medium 1 Sections

We often encounter large and complex networks during our assessments. We must be comfortable approaching an internal or external network, regardless of the size, and be able to work through each phase of the penetration testing process to reach our goal. This module will guide students through a simulated penetration testing engagement, from start to finish, with an emphasis on hands-on testing steps that are directly applicable to real-world engagements.

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