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MacOS Fundamentals

This module covers the fundamentals required to work comfortably within the macOS operating system and shell.

4.53

Created by 21y4d
Co-Authors: Sentinal

Fundamental General

Summary

DISCLAIMER: This module requires access to a macOS machine for completion. Refer to the end of this page for more details.

macOS is a staple in many environments and businesses, such as academia, content creation, and audio/visual shops worldwide. Furthermore, macOS makes for an excellent pentesting OS and is very popular among pentesters and developers alike, for its security and ability to natively run pentesting tools as well as simulate other OS's through virtual machines.

Understanding how to navigate the file system and the command line is essential for effective enumeration, privilege escalation, lateral movement, post-exploitation, and defense. When set up correctly, we can even use macOS as our attack box during assessments. With advances in centralized administration, we are starting to see macOS hosts within Active Directory environments as well more frequently. This module covers the essentials for starting with the macOS operating system and command line.

This module will provide a quick history lesson on the origins of macOS and its architecture and then guide us through utilizing and administering all it has to offer. We will practice using the Graphical User Interface (GUI) along with the Command-line Interface (CLI) to administer many different portions of the host, including:

  • System settings and preferences
  • Filesystem navigation and usage
  • Networking concepts as they pertain to macOS
  • Application and update control via native apps and the use of Homebrew
  • Security considerations to include host hardening and monitoring

Furthermore, this module will cover the following:

  • macOS system structure
  • File system specifics
  • Permissions management
  • macOS services and applications
  • Interacting with the operating system (CLI & GUI)
  • Security Considerations
  • Application management

This module is broken down into sections with accompanying hands-on exercises to practice the tactics and techniques we cover.

You can start and stop the module anytime 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 "Fundamental" and assumes that the student has a basic knowledge of the macOS operating system from a casual user perspective.

To complete this module, you must have access to a macOS machine (e.g., MacBook/Mac Mini/Mac Pro). If you do not have access to a Mac, you may still take the module and go through it to understand the macOS fundamentals, though you will not be able to practice the provided exercises within the module. Furthermore, the module may require basic terminal usage, mostly covered in the Linux Fundamentals module, so we recommend doing that module before this one.

What Is macOS?


Many have and use an Apple product in their lives every day. From your Macbook to your iPhone or iPad, there are many different revisions to the Apple OS line, but most of them are, in fact, based on macOS (originally Mac OS X). So let's answer the question, "What is macOS?"

Let's start this module by breaking down the history of macOS, its use, architecture, and core components. macOS is the official term for the operating system used on Apple computers. It is a widely used OS and is second in market use only to Windows operating systems. It can be found in the realms of daily home use, business management, graphical design, and arts.


History Roundup

Let's take a look at the origins of macOS for a minute.

Timeline

2000-2002

This is known as the original start to OS X leading up to macOS as we know it. In the fall of 2000, Apple released a public beta code named Kodiak for users to test and provide feedback. After taking in those responses and making fixes, Apple released Mac OS X (10.0), named Cheetah, in the spring of 2001. This is the first time the world will see the new User interface Aqua.
A few months later, Apple released OS X (10.1) named Puma. This iteration drastically improved system performance and began officially replacing Mac OS 9, OS X's predecessor, on all new computers shipped out.
In the Fall of 2002, the next iteration of OS X was released. OS X (10.2), named Jaguar, focused on user interaction improvements and introduced new applications like iChat to the world.

2003

OS X (10.3) named Panther was released in the fall of 2003. Most interesting about this release was the fact that Apple's new web browser Safari replaced Internet Explorer on their hosts. Support for integration with Active Directory was also added during this release.

2005

OS X (10.4) named Tiger released, bringing with it new features and new looks with Widgets and dashboards. Up to this point, only PowerPC processors were supported for Apple products. With this release, Apple hit a milestone by officially releasing support for the Intel based chipset in their hosts.

2007-2009

2007 was a big year for Apple. In the spring, they unveiled their new gadget that changed the world, the iPhone and with it iOS, which was completely based on Mac OS X. That same year in the fall, OS X (10.5) Leopard was released and introduced Apple's built-in backup system, Time Machine, along with support for 64-bit applications. At this point, dual-booting was first introduced to the Mac line with the introduction of Boot Camp, providing support for the Windows OS on Mac hardware.
Following Leopard in 2009, OS X (10.6) Snow Leopard released, which was an incremental update over Leopard. The only real changes were the addition of the AppStore and the discontinuation of support for the PowerPC processors. From this point on, Apple moved to Intel based processors exclusively.

2011-2012

OS X (10.7) Lion brought many successful features from iOS to their Mac OS X, like Gestures and saved window states. Lion also saw the introduction of iCloud to Mac OS X, bringing interconnected cloud storage to the Apple realm of products.
2012 brought us Mountain Lion (10.8), with the main focus on bringing many of the features that were currently iOS-only into Mac OS X.

2013

From this point forward, Apple decided to stick to a yearly release cycle of Mac OS X. After over a decade of releases named after big wild cats, Apple also decided to ditch the animal theme and move to a naming convention based off locations and landmarks within California.. With a fresh new naming standard, OS X (10.9) Mavericks, kicks off the new release schedule and Apple put out a statement that all future releases would be free for upgrade (including this one). There were some functionality tweaks but nothing substantial under the hood.

2014-2015

With the release of OS X (10.10) Yosemite, the Handoff functionality brought exciting change to the Apple product lines allowing users to seamlessly move any task users are working on from one Apple device to another. The UI is moving more toward the iOS look and feel.
OS X (10.11) El Capitan brought more performance changes and the ability to tile your screen with split views.

2016-2017

OS X is dead! Long live macOS. With the release of macOS (10.12) named Sierra, Apple officially moved away from the "OS X" moniker to "macOS". Along with this change, Apple brought integration for Siri, Apply Pay, and other tweaks under the hood to macOS.
macOS (10.13) High Sierra brought along the switch to the Apple File System (APFS) and several other support functionalities under the hood.

2018

macOS (10.14) Mojave brought significant visual enhancements with this update. Darkmode was introduced to the platform, working natively with all macOS apps and many third-party ones. The ability to have your host dynamically shift from dark mode to light mode with the time of day was also a big change. Mojave also ported over several more iOS apps to macOS, like News, Stocks, and Home, to name a few.

2019

macOS (10.15) Catalina split iTunes into three separate apps (Apple TV, Podcasts, and Music). This update also focused on bringing more iOS features to macOS and also allowed the use of an iPad as a secondary display with the Sidecar feature.

2020

macOS 11 releases, named Big Sur, finally moved away from OS version 10 (or X) and brought big changes to the UI and functionality of the OS as a whole. Much care was taken to improve communications channels in this revision as well. The major new feature of macOS 11 was supporting the all-new Apple Silicon processor while still supporting Intel processors for at least a few more years. Much of the focus of this revision also went to bug fixes.

2021

macOS 12 Monterey. Integration improvements, dubbed Universal Control, were introduced that made controlling multiple Apple devices at once much more seamless. AirPlay saw some big changes, and you can now use a Mac as a speaker when casting to other devices. Spatial Audio was introduced to Facetime, along with other features like SharePlay which, allow you to share audio, video, and even your screen with other users over FaceTime.

2022

macOS 13 Ventura is the most recent release of macOS as of the time of writing this module. It introduced a new window management feature called Stage Manager, along with other features like Continuity Camera, new Apps and app updates, a facelift to the settings app, along with other features.


Now that we know a bit about the history of macOS let's dive into the architecture of the OS itself and some of its core components.


OS & Architecture Info

Kernel: XNU

  • The Mach kernel is the basis (along with portions from BSD) of the macOS and iOS XNU Kernel architecture, which handles our memory, processors, drivers, and other low-level processes.

OS Base: Darwin, a FreeBSD Derivative open-sourced by Apple.

  • Darwin is the base of the macOS operating system. Apple has released Darwin for open-source use. Darwin, combined with several other components such as Aqua, Finder, and other custom components, make up the macOS as we know it.

As mentioned above, macOS recently shifted to mainly support Apple Silicon while still supporting Intel processors for the time being.

These points above make up the basis of macOS as an operating system. There is much more to it, but we are just trying to get an initial understanding of what macOS is for now. Next, let us address several core components within macOS.


Core Components

GUI: Aqua is the basis for the Graphical interface and visual theme for macOS. As technology has advanced, so has Aqua, providing more and more support for other displays, rendering technologies, and much more. It is known for its flowy style, animations, and transparency with windows and taskbars.

File Manager: Finder is the component of macOS that provides the Desktop experience and File management functions within the OS. Aqua is also responsible for the launching of other applications.

Application Sandbox: By default, macOS and any apps within it utilize the concept of sandboxing, which restricts the application's access outside of the resources necessary for it to run. This security feature would limit the risk of a vulnerability to the application itself and prevent harm to the macOS system or other files/applications within it.

Cocoa: Cocoa is the application management layer and API used with macOS. It is responsible for the behavior of many built-in applications within macOS. Cocoa is also a development framework made for bringing applications into the Apple ecosystem. Things like notifications, Siri, and more, function because of Cocoa.


Now that we have a general idea of what macOS is, its origins, and what it is comprised of, let's move on to explore the user interface and all it entails.

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Relevant Paths

This module progresses you towards the following Paths

DFeD Required Training

These courses have been identified as foundational learning for all DFeD members. Content covers the basics behind Windows, Linux, and macOS operating systems, as well as Active Directory, networking, and web applications.

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Medium
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Microsoft Active Directory (AD) has been, for the past 20+ years, the leading enterprise domain management suite, providing identity and access management, centralized domain administration, authentication, and much more. Throughout those years, the more integrated our applications and data have become with AD, the more exposed to a large-scale compromise we have become. In this module, we will walk through the most commonly abused and fruitful attacks against Active Directory environments that allow threat actors to perform horizontal and vertical privilege escalations in addition to lateral movement. One of the module's core goals is to showcase prevention and detection methods against the covered Active Directory attacks.

Operating System Fundamentals

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Easy Path Sections 55 Sections
Required: 30
Reward: +30
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Reward: +10
This module covers the fundamentals required to work comfortably with the Linux operating system and shell.
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This module covers the fundamentals required to work comfortably within the macOS operating system and shell.

Especialista de Riesgos de Ingenieria

Plan de capacitación gestión 2024

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Required: 6920
Reward: +1480
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Fundamental
Path Sections 21 Sections
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Path Sections 30 Sections
Reward: +10
This module covers the fundamentals required to work comfortably with the Linux operating system and shell.
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Path Sections 14 Sections
Reward: +10
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Reward: +10
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Path Sections 11 Sections
Reward: +10
This module covers the fundamentals required to work comfortably within the macOS operating system and shell.
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Path Sections 14 Sections
Reward: +10
Automating tedious or otherwise impossible tasks is highly valued during both penetration testing engagements and everyday life. Introduction to Python 3 aims to introduce the student to the world of scripting with Python 3 and covers the essential building blocks needed for a beginner to understand programming. Some advanced topics are also covered for the more experienced student. In a guided fashion and starting soft, the final goal of this module is to equip the reader with enough know-how to be able to implement simple yet useful pieces of software.
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.
Easy
Path Sections 10 Sections
Reward: +10
This module covers the basics needed for working with Bash scripts to automate tasks on Linux systems. A strong grasp of Bash is a fundamental skill for anyone working in a technical information security role. Through the power of automation, we can unlock the Linux operating system's full potential and efficiently perform habitual tasks.
Medium
Path Sections 11 Sections
Reward: +10
As a penetration tester or red teamer, it is imperative that we understand the tools that we use inside and out and also have the ability to write out own, even simple, tools if we are on an assessment with certain constraints such as no internet or the requirement to use a customer provided host as our "attack box." A strong understanding of DNS as well as the various ways to interact with fundamental when performing any security assessment.
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.
Easy
Path Sections 6 Sections
Reward: +10
Bug bounty programs encourage security researchers to identify bugs and submit vulnerability reports. Getting into the world of bug bounty hunting without any prior experience can be a daunting task, though. This module covers the bug bounty hunting process to help you start bug bounty hunting in an organized and well-structured way. It's all about effectiveness and professionally communicating your findings.
Medium
Path Sections 8 Sections
Reward: +20
Dive into Windows digital forensics with Hack The Box Academy's "Introduction to Digital Forensics" module. Gain mastery over core forensic concepts and tools such as FTK Imager, KAPE, Velociraptor, and Volatility. Dive deep into memory forensics, disk image analysis, and rapid triaging procedures. Learn to construct timelines from MFT, USN Journals, and Windows event logs while getting hands-on with key artifacts like MFT, USN Journal, Registry Hives, Prefetch Files, ShimCache, Amcache, BAM, and SRUM data.
Medium
Path Sections 6 Sections
Reward: +20
This module initially lays the groundwork for understanding Threat Hunting, ranging from its basic definition, to the structure of a threat hunting team. The module also dives into the threat hunting process, highlighting the interrelationships between threat hunting, risk assessment, and incident handling. Furthermore, the module elucidates the fundamentals of Cyber Threat Intelligence (CTI). It expands on the different types of threat intelligence and offers guidance on effectively interpreting a threat intelligence report. Finally, the module puts theory into practice, showcasing how to conduct threat hunting using the Elastic stack. This practical segment uses real-world logs to provide learners with hands-on experience.
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.
Medium
Path Sections 6 Sections
Reward: +20
This module provides a comprehensive introduction to Splunk, focusing on its architecture and the creation of effective detection-related SPL (Search Processing Language) searches. We will learn to investigate with Splunk as a SIEM tool and develop TTP-driven and analytics-driven SPL searches for enhanced threat detection and response. Through hands-on exercises, we will learn to identify and understand the ingested data and available fields within Splunk. We will also gain practical experience in leveraging Splunk's powerful features for security monitoring and incident investigation.
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.
Easy
Path Sections 13 Sections
Reward: +20 NEW
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.
Medium
Path Sections 14 Sections
Reward: +20
This module covers the fundamentals of password cracking using the Hashcat tool.
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.
Medium
Path Sections 19 Sections
Reward: +20 NEW
A backend that handles user-supplied input insecurely can lead to devastating security vulnerabilities such as sensitive information disclosure and remote code execution. This module covers how to identify and exploit server-side bugs, including Server-Side Request Forgery (SSRF), Server-Side Template Injection (SSTI), and Server-Side Includes (SSI) injection attacks.
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.
Medium
Path Sections 11 Sections
Reward: +20
This module offers an in-depth exploration of Suricata, Snort, and Zeek, covering both rule development and intrusion detection. We'll guide you through signature-based and analytics-based rule development, and you'll learn to tackle encrypted traffic. The module features numerous hands-on examples, focusing on the detection of prevalent malware such as PowerShell Empire, Covenant, Sliver, Cerber, Dridex, Ursnif, and Patchwork. We also dive into detecting attacking techniques like DNS exfiltration, TLS/HTTP Exfiltration, PsExec lateral movement, and beaconing through IDS/IPS.
Easy
Path Sections 11 Sections
Reward: +20
This module provides a concise yet comprehensive overview of Security Information and Event Management (SIEM) and the Elastic Stack. It demystifies the essential workings of a Security Operation Center (SOC), explores the application of the MITRE ATT&CK framework within SOCs, and introduces SIEM (KQL) query development. With a focus on practical skills, students will learn how to develop SIEM use cases and visualizations using the Elastic Stack.
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.
Easy
Path Sections 11 Sections
Reward: +20
This Hack The Box Academy module covers how to create YARA rules both manually and automatically and apply them to hunt threats on disk, live processes, memory, and online databases. Then, the module switches gears to Sigma rules covering how to build Sigma rules, translate them into SIEM queries using "sigmac", and hunt threats in both event logs and SIEM solutions. It's all hands-on, using real-world malware and techniques.
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.
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.
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.
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.
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.
Medium
Path Sections 20 Sections
Reward: +100
This module serves as a follow-up to the Game Hacking Fundamentals module. You will learn how to persist Cheat Engine Scripts by scanning for byte arrays, editing game assemblies, utilising runtime hooking to modify games, and tampering with game network traffic using Burp.
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.
Hard
Path Sections 18 Sections
Reward: +100
This module provides a detailed overview of Supply Chain Attacks, covering hardware and software aspects. It explores the impact of supply chains, the lifecycle of attacks, specific vulnerabilities, and mitigation strategies.
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.
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.