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Mastering Windows Security and Hardening
Mastering Windows Security and Hardening

Mastering Windows Security and Hardening: Secure and protect your Windows environment from intruders, malware attacks, and other cyber threats

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Profile Icon Mark Dunkerley Profile Icon Matt Tumbarello
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Mastering Windows Security and Hardening

Chapter 1: Fundamentals of Windows Security

Nowadays, the conversation of cybersecurity has become a hot topic throughout the world. And even more so with leadership teams and board members of many major organizations asking the question, are we secure? The short answer is no: no one is secure in today's digital world, and there has never been a more critical time to ensure that you are doing everything within your power to protect your organization and its users.

As we continue to receive daily news of breaches throughout the world, it is clear how severe the issue of cybercrime has become. To put it bluntly, we simply need to do a better job of protecting the data that we collect and manage within our organizations today. This isn't an easy task, especially with the advancement of organized cyber and state-sponsored groups with budgets, most likely, far exceeding that of most organizations. As security professionals, we need to do our due diligence and ensure we identify all risks within the organization. Once identified, they will need to be addressed or accepted as a risk by leadership.

As a consumer, it is most likely that your data has already been breached, and there's a chance your account information and passwords are sitting on the dark web somewhere. We need to work with the assumption that our personal data has already been breached and build better barriers around our data and account information. For example, in the U.S., purchasing identity protection as a service to monitor your identity can serve as an insurance policy if you incur any damages. In addition to this, the ability to place your credit reports on hold to prevent bad actors from opening accounts under your name is another example of a defensive approach that you can take to protect your personal identity.

As the cybersecurity workforce continues to evolve and strengthen with more and more talented individuals, we want to help contribute to the importance of securing our data, and we hope this book provides you with the necessary knowledge to do the right thing for your organization. As you read this book, you will not only learn the technical aspects of securing Windows, but you will also learn what else is necessary to ensure the protection of Windows and the users that use it. Protecting Windows has become a lot more than making a few simple configuration changes and installing an antivirus (AV) tool. There is an entire ecosystem of controls, tools, and technology to help protect your Windows systems and users.

As you read through this chapter, you will learn about the broader fundamentals of security and the principles behind the foundation that is needed to protect your Windows environment. Specifically, you will learn about the following:

  • An overview of the security transformation within the industry
  • A look at security trends as they relate to today's digital world
  • A review of the current threat landscape and common vulnerabilities
  • An overview of some recent publicly known breaches
  • An overview of the current security challenges faced today
  • What Zero Trust security is, and why we need to adopt this approach moving forward

Understanding the security transformation

Over the years, security has evolved from being just a shared role or a role that didn't even exist within a business. Today, well-defined teams and organizational structures do actually exist or are being created to focus solely on security. Not only are these teams maturing constantly, but the Chief Information Security Officer (CISO) has become a person of significant importance who may report directly to a Chief Executive Officer (CEO) within an organization and not the CIO.

Over the years, many roles that never existed before have begun to appear within the security world, and new skill sets are always in demand. As an overview, the following is a list of some of the more common security roles that you can expect to see within a security program: 

  • CISO/CSO (Chief Information Security Officer/Chief Security Officer)
  • IT Security Director
  • IT Security Manager
  • Security Architect/Engineer
  • Security Analyst
  • Security/Compliance Officer
  • Security Administrator
  • Security Engineer
  • Software/Application Security Developer
  • Software/Application Security Engineer
  • Cryptographer/Cryptologist
  • Security Consultant/Specialist
  • Network Security Engineer
  • Cloud Security Architect

One thing to point out, in regard to these roles, is the major shortage of the cybersecurity workforce throughout the world. A cybersecurity workforce study by (ISC)² shows that a worldwide growth of 145% is needed to meet the demand for cyber experts. In the US, this number needs to grow by 62%. These numbers clearly show the demand for skilled cybersecurity experts along with opportunities for growth. The challenge with this growth is that new positions are continuously being created as new skills are needed, which makes it difficult to find well-seasoned talent (read more about the (ISC)² 2019 Cybersecurity Workforce Study here: https://www.isc2.org/Research/Workforce-Study).

One of the primary factors for the growing need of security experts correlates to the advancement of the PC (or personal computer) and its evolution throughout the years. The PC has changed the way we connect. And, with this evolution comes the supporting infrastructure, which has evolved into many data centers seen throughout the world.

As we are all aware, Windows has been the victim of numerous vulnerabilities over the years and continues to be a victim even today. The initial idea behind the Windows Operating System (OS) was a strong focus on usability and productivity. As a result of its success and adoption across the globe, it became a common target for exploits. This, in turn, created many gaps in the security of Windows that have traditionally been filled by many other companies. A good example is a need for third-party AV software. As the world has turned more toward digitization over the years, and the adoption of Windows usage has continued to grow, so has the need for improved security along with dedicated roles within this area. Protecting Windows has not been an easy task, and it continues to be an ongoing challenge.

Living in today's digital world

Today, we are more reliant on technology than ever and live in a world where businesses cannot survive without it. As our younger generations grow up, there is greater demand for the use of advanced technology. One scary thought is how fast the world has grown within the previous 100 years compared to the overall history of mankind. Technology continues to push the boundaries of innovation, and a significant portion of that change must include the securing of this technology. Especially since the world has become a more connected place with the advancement of the internet.

To give you a rough idea of technology usage today, let's take a look at the current desktop usage throughout the world. For these statistics, we will reference an online service, called Statcounter GlobalStats: https://gs.statcounter.com/. This dataset is not all-inclusive, but there is a very large sampling of data used to give us a good idea of worldwide usage. Statcounter GlobalStats collects its data through web analytics via tracking code on over 2 million websites globally. The aggregation of this data equates to more than 10 billion page views per month. The following screenshot shows the OS market share that is in use worldwide. More information from Statcounter can be viewed at https://gs.statcounter.com/os-market-share/desktop/worldwide:

Figure 1.1 – Statcounter Desktop Operating System Market Share Worldwide

Figure 1.1 – Statcounter Desktop Operating System Market Share Worldwide

As you can see, the Windows desktop market is more widely adopted than any other OS available today. Seemingly, Windows has always had negative connotations because of its ongoing vulnerabilities in comparison to other OSes. Part of this is due to how widely used Windows actually is. A hacker isn't going to waste their time on an OS that isn't widely adopted. We can assume there would be a direct correlation between OS adoption rates and available security vulnerabilities. Additionally, the Windows OS is supported across many types of hardware, which opens up opportunities for exploits to be developed. One reason as to why we see significantly fewer macOS vulnerabilities is due to the hardware control with which Apple allows its software to run. As the platform has grown, though, we have seen an increase of vulnerabilities within its OS too. The point we're making is that we tend to focus our efforts on areas where it makes sense, and Windows has continued to be a leader in the desktop space, making it a very attractive source to be attacked. This, in turn, has created an ecosystem of vendors and products over the years, all aimed at helping to protect and secure Windows' systems.

Let's take a look at the current adoption of the different Windows OSes in use. The following screenshot from Statcounter shows the current Windows desktop version usage around the world today. To view these statistics, visit https://gs.statcounter.com/os-version-market-share/windows/desktop/worldwide:

Figure 1.2 – Desktop Windows Version Market Share Worldwide

Figure 1.2 – Desktop Windows Version Market Share Worldwide

As you can see, Windows 10 has become the most adopted OS. Microsoft continues to push more users and organizations to Windows 10, and this is where they spend the majority of their development resources. There are also major changes to Windows 10 compared to older versions, which is why it is critical to migrate from older versions, especially for security-specific reasons. Microsoft ended its support (including security updates) for Windows XP in April 2014 and Windows 7 in January 2020.

NetMarketShare is another analytical site similar to Statcounter GlobalStats with its own set of statistics for reference: https://netmarketshare.com/.

A recent buzz term you have most likely heard in recent years is that of digital transformation. This refers to the shift from a legacy on-premises infrastructure to a modernized cloud-first strategy to support the evolving need of big data, machine learning, Artificial Intelligence (AI), and more. A significant part of this shift also falls within Windows systems and management. In Chapter 3, Server Infrastructure Management, we will look at the differences between a data center and a cloud model, including where the responsibilities fall for maintaining and securing underlying systems. Prior to digital transformation, we relied heavily on the four walls of the corporation and its network to protect a data center and its systems. This included a requirement for client devices to be physically on the corporate network in order to access data and services. With this model, our devices were a little easier to manage and lock down, as they never left the corporate office. Today, the dynamics have changed, and, referencing back to Statcounter in the following screenshot, you can see a significant shift from traditional desktop usage to a more mobile experience and requirement. To view the source of this diagram, visit https://gs.statcounter.com/platform-market-share/desktop-mobile-tablet/worldwide/#monthly-200901-202003:

Figure 1.3 – Statcounter platform comparison Jan 2009 – Jan 2020

Figure 1.3 – Statcounter platform comparison Jan 2009 – Mar 2020

Focusing on Windows security, the traditional model of an organization would have typically included the following security tools as part of its baseline:

  • AV (antivirus software)
  • Windows Firewall
  • Internet proxy service
  • Windows updates

Depending on your organization or industry, there may have been additional tools. However, for the most part, I'd imagine the preceding list was the extent of most organizations' security tools on Windows client devices. The same would have most likely applied to the Windows servers in the traditional model. As this digital transformation has brought change, the traditional method of Windows management has become a legacy. There is an expectation that we can work and access data from anywhere at any time. We live in an internet-connected world, and, when we plug our device in, we expect to access our data with ease. With this shift, there is a major change in the security of the systems we manage and, specifically, the Windows server and client. As we shift our infrastructure to the cloud and enable our users to become less restricted, the focus of security revolves not only around the device itself but that of the user's identity and, more importantly, the data. Today, the items that we listed earlier will not suffice. The following tools are those that would be needed to better protect your Windows devices:

  • Advanced Threat Protection (ATP): AV and threat protection, advanced analytics and behavioral monitoring, network protection, exploit protection, and more
  • Advanced data loss prevention
  • Information protection
  • Identity protection: biometric technology, multi-factor authentication, and more
  • Application control
  • Machine learning and advanced AI security services
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Description

Are you looking for effective ways to protect Windows-based systems from being compromised by unauthorized users? Mastering Windows Security and Hardening is a detailed guide that helps you gain expertise when implementing efficient security measures and creating robust defense solutions. We will begin with an introduction to Windows security fundamentals, baselining, and the importance of building a baseline for an organization. As you advance, you will learn how to effectively secure and harden your Windows-based system, protect identities, and even manage access. In the concluding chapters, the book will take you through testing, monitoring, and security operations. In addition to this, you’ll be equipped with the tools you need to ensure compliance and continuous monitoring through security operations. By the end of this book, you’ll have developed a full understanding of the processes and tools involved in securing and hardening your Windows environment.

Who is this book for?

This book is for system administrators, cybersecurity and technology professionals, solutions architects, or anyone interested in learning how to secure their Windows-based systems. A basic understanding of Windows security concepts, Intune, Configuration Manager, Windows PowerShell, and Microsoft Azure will help you get the best out of this book.

What you will learn

  • Understand baselining and learn the best practices for building a baseline
  • Get to grips with identity management and access management on Windows-based systems
  • Delve into the device administration and remote management of Windows-based systems
  • Explore security tips to harden your Windows server and keep clients secure
  • Audit, assess, and test to ensure controls are successfully applied and enforced
  • Monitor and report activities to stay on top of vulnerabilities
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Table of Contents

18 Chapters
Section 1: Getting Started Chevron down icon Chevron up icon
Chapter 1: Fundamentals of Windows Security Chevron down icon Chevron up icon
Chapter 2: Building a Baseline Chevron down icon Chevron up icon
Chapter 3: Server Infrastructure Management Chevron down icon Chevron up icon
Chapter 4: End User Device Management Chevron down icon Chevron up icon
Section 2: Applying Security and Hardening Chevron down icon Chevron up icon
Chapter 5: Hardware and Virtualization Chevron down icon Chevron up icon
Chapter 6: Network Fundamentals for Hardening Windows Chevron down icon Chevron up icon
Chapter 7: Identity and Access Management Chevron down icon Chevron up icon
Chapter 8: Administration and Remote Management Chevron down icon Chevron up icon
Chapter 9: Keeping Your Windows Client Secure Chevron down icon Chevron up icon
Chapter 10: Keeping Your Windows Server Secure Chevron down icon Chevron up icon
Section 3: Protecting, Detecting, and Responding for Windows Environments Chevron down icon Chevron up icon
Chapter 11: Security Monitoring and Reporting Chevron down icon Chevron up icon
Chapter 12: Security Operations Chevron down icon Chevron up icon
Chapter 13: Testing and Auditing Chevron down icon Chevron up icon
Chapter 14: Top 10 Recommendations and the Future Chevron down icon Chevron up icon
Other Books You May Enjoy Chevron down icon Chevron up icon

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Umdeya Aug 13, 2020
Full star icon Full star icon Full star icon Full star icon Full star icon 5
This book highlights even the little stuff we may forget to enforce and implement as ICT security professionals. A must-read for security professional in a windows environment. C.P.
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AL Oct 11, 2020
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Matt Tumbarello (author) changed by life, this book helped me through hard times. I figured out how to harden my windows and master it. It changed me from an emo to a nerd overnight. 10/10 stars would recommend to emos
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Jeffrey McCrae Oct 11, 2022
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The book is a awesome road map for the protection of Windows severs against cyber threats!!!!!
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Senai Ahderom Jul 09, 2020
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Great book. It covers how to efficiently create security measures and harden for the Modern Enterprise. Good combination of conceptual and practical advice and covers Azure/Microsoft Intune and Config Manager.
Amazon Verified review Amazon
Anslem John Aug 07, 2020
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This is great book for any Sys Admin that manages a Windows based environment . It starts off highlighting how the security posture in organisations have changed and how it has affected Admins ability to protect any windows client\sever environment.This book has covered all the major areas : from developing standards and procedures, all the way to using the M365 Security Center and more. What I also like about this book is that it applies real world scenarios. At no point did I feel any of my environments I have secured were unique and therefore what the book offers is not applicable. Straight away you can apply what was learnt.This is a must have book for any Sys Admin, Security Admin etc!
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