Complete Guide to Windows Server + Compare Differences

By Staff Contributor on April 8, 2020

Servers provide functionality for other networked computers, and as such their operating systems differ from those run on regular computers. Windows Server by Microsoft is a leader in server operating systems, having released many Windows Server versions over the years, and it’s become the main rival for Linux.

This guide provides information for network administrators looking to understand the difference between Windows Server versions. It includes specifics for the different Windows Server editions up to the latest release of Windows Server 2019. I’ll also explain what to look for in a Windows server monitoring tool like SolarWinds® Server & Application Monitor to help you get the most out of your server performance.

Windows NT Servers

The Evolution of Windows Server

Specialized Editions of Windows Server
Best Windows Server Monitoring Software
Implementing Windows Server

Windows Server compare guide

Windows NT Servers

The Windows Server operating system was first introduced in the 1990s, and Microsoft branded it with “NT” (short for “New Technology”) up until the year 2000. The company had several releases of the NT version of the operating system, as follows:

Windows NT 3.1

The original release of the Windows NT server was not version 1. Instead, it was Windows NT Advanced Server 3.1, with the release numbering designed to match the version of the standard operating system at the time.

This first release came out in 1993 as a 32-bit system and was developed to support new server hardware. This began the evolution of the Windows Server line of operating systems.

Windows NT 3.5

The next version, Windows NT Server 3.5, was released in 1994. This version enhanced the server functionality to support interconnectivity with both Unix systems and Novell NetWare. Because Unix and Novell servers were the standards at the time, this approach was essential for Windows NT Server to be competitive in the market. The interconnectivity meant servers with the Windows operating system could be incorporated in an existing network running on Unix or Novell.

Windows NT 3.51

Windows NT Server 3.51 came out in 1995 to align with the regular operating system release of Windows 95. The server version supported computers running Windows 95 and provided some improvements to make the system more stable. The upgrade also provided the ability to manage the software licenses on client computers, including installing and updating operating system elements on client computers over the network.

Windows NT 4.0

Although Microsoft released a server version alongside Windows 95, the user interface for the operating system didn’t match the Windows 95 look and feel until 1996, when Windows NT Server 4.0 was released.

One of the most important components of the 4.0 release was Microsoft Internet Information Services (IIS). This free addition is now the most popular web management software in the world. Apache HTTP Server is in second place, although up until 2018, Apache was the leading web server software.

Windows NT Server had additional service packs to support increasingly complicated networks, and this led to the release of Windows NT 4.0 Enterprise Server in 1997. The Microsoft Transaction Server and Message Queue enhancements were designed to handle interactions with congested networks. The updates also added the ability to manage operating systems for server clusters and provided integration for public-key encryption services.

Finally, in 1998, Windows NT 4.0 Terminal Server Edition came out. This was the last enhancement to the NT operating system series, and it provided a bridge for 16-bit DOS applications to interface with 32-bit desktop environments. The release also supported connections with non-Windows systems.

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The Evolution of Windows Server

In 2000, the branding for Windows servers changed. Microsoft dropped the “NT” and released Windows Server 2000 to highlight its relevance for modern systems. After that, the server versions were named based on the year each edition was released.

Windows Server 2000

Windows Server 2000 provided the initial functionality for many features of the operating system still in use today. The main features included:

  • XML support
  • Active Server Pages creation
  • Active Directory use for user authentication

The release also included specialized versions for different server environments, with Advanced Server and Datacenter Server editions as well as the standard Windows Server operating system.

Windows Server 2003

The release of Windows Server 2003 brought a significant rewrite to the server software. The main goal of the change was to reduce the need to reboot the system, specifically by providing the ability to install updates and patches without needing to restart.

With Windows 2003, Microsoft provided updates to the security features. This was also the first time the company included the .NET framework in the server operating system.

Another major addition with the 2003 release was the ability to define server roles. This allowed the operating system to be customized for specific tasks, like a DNS server. Microsoft also provided multiple versions of the release, including the Standard, Advanced, and Datacenter versions, and a new Windows Server 2003 Web Edition meant for internet servers. Another update came out not long after the initial release to convert the Windows Server system to a 64-bit environment.

Windows Server 2003 R2

In 2005, Windows Server 2003 R2 came out as a free upgrade to the Windows Server 2003 edition. Once this release was available, all Windows Server 2003 sales were for Windows Server 2003 R2.

This release focused on enhanced security, especially user authentication. This was based on Active Directory, which remains the foundation for user authentication today. The R2 release also included a new feature, Active Directory Federation Service. This gave network administrators more flexibility when managing server permissions, such as the ability to include external devices when enabling “single sign-on” permissions.

The upgrade for Active Directory also added Active Directory Application Mode. This gave users access to third-party applications without going through all the authentication steps for the external software, as long as the users were verified through the Active Directory extension.

Another security feature of R2 was the Security Configuration Wizard, which provided the ability to define security policies for groups of computers. Additionally, Windows Server 2003 R2 contained improved data compression for transfers and files and multi-site WAN replication procedures.

Windows Server 2008

Microsoft took another three years to develop significant updates to Windows Server, which were released as Windows Server 2008. This release saw more improvements to Active Directory and changes in the interaction between the operating system’s software support features and network services.

A major enhancement came with Microsoft’s Hyper-V system. This virtualization product allowed Windows Server users to create virtual machines (VMs), which was increasingly important to IT teams. This may have been included for competitive reasons, to prevent Windows users from looking elsewhere for a VM system.

Windows Server 2008 included new software administration tools called Event Viewer and Server Manager. These utilities gave administrators more control over important server activities.

A different version of the Windows Server software was available with Server Core. This bare-bones version of the software, without the standard graphical user interface (GUI), provided command-line access to the server. This was a welcome change for administrators who were more familiar with Unix and Linux systems with existing command-line environments, and it made Windows Server an important competitive product for Microsoft.

Windows Server 2008 had Standard, Enterprise, Datacenter, and Web versions.

Windows Server 2008 R2

An update to the 2008 edition came out in 2009 as Windows Server 2008 R2, and it’s still used today. The major change with this version involved the transition from being based on Windows Vista to being based on Windows 7. This brought the system to a 64-bit environment.

Many of the other updates were technical and not very visible to users, since they focused on supporting services. The release saw additional updates to Active Directory, this time in support of better group policy implementation.

Windows Server 2008 R2 also included some new services, such as Remote Desktop Services, or RDS, which repackaged Terminal Services. Additionally, DirectAccess and BranchCache were introduced, designed to provide better server access to users in remote locations.

Windows Server 2012

In 2012, Microsoft added new functionality to Windows Server 2012 to become competitive in the cloud, and even marketed the new version as “Cloud OS.”

These updates focused on improving the Hyper-V functionality, so it could be integrated into both local hosts and onsite delivery. This allowed the Hyper-V architecture to be easily used with other new cloud technologies.

Specific changes to support this included:

  • Updates to the storage system, which is mediated by Hyper-V
  • Addition of the Hyper-V virtual switch
  • Inclusion of Hyper-V Replica

PowerShell and Server Core were also updated with the release. The other major change was a new Essentials edition aimed at smaller, networked businesses. In total, Windows Server 2012 had four editions: Essentials, Foundation, Standard, and Datacenter.

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Windows Server 2012 R2

Windows Server 2012 R2 was released as an update to the prior release just a year later, in 2013. Many of the changes were improvements to functions needed to integrate with cloud services. This included rewrites to both security protocols and network services.

The release also saw more updates to PowerShell, among them the introduction of the Desired State Configuration system. This enhanced the management of network configurations.

Another change involved improved functionality for storage systems, including better access for file sharing and replication of distributed files. Web services were also enhanced, as were visualization systems.

One major change came with the ability to serve software to mobile devices, which was important with the increased use of tablets.

Windows Server 2016

The next release was Windows Server 2016, and it came with a new server option, Nano Server. This was a scaled-down server implementation with limited interfaces, making it more secure from attacks.

Another introduction with this release was Network Controller. This console program gave administrators the ability to manage all network devices, whether physical or virtual, from a single location.

To support the use of containers, VM systems were enhanced to interact with Docker and to support encryption for Hyper-V. Additionally, the release included Server Core.

The Windows Server 2016 release only had Standard and Datacenter editions, and it did not have a follow-up R2 version.

Windows Server 2019

The most current Windows Server version is Windows Server 2019. It was released in October 2018 and included several important new features to meet growing networking requirements:

  • Windows Admin Center: Formerly called Project Honolulu, Windows Admin Center was designed to provide a central location for server management. The utility includes many of the tools administrators use daily, among them configuration management, performance monitoring, and management of services running on different servers.
    Windows Admin Center can be used with Windows Server 2019 but is also backward compatible with Windows Server 2016 and Windows Server 2012 R2. Additionally, the utility supports servers even if they have different operating systems.
  • Hyperconverged Infrastructure (HCI): Microsoft had been moving to greater virtualization since the inclusion of Hyper-V in the Windows Server 2008 release. The latest version includes all the VM improvements since the initial release, providing a true HCI.
    These HCI features give network administrators the ability to manage virtualized services more simply, without even having to take down the system. Additionally, resources supporting VMs can be adjusted automatically, streamlining management even further.
    With Windows Server 2019, HCI can support both software-defined data centers and their customers.
  • Windows Subsystem for Linux: Even before this release, Linux could be run on a Windows server by using a VM. With Windows Server 2019, though, Microsoft provided a subsystem compatible with Linux, called “native shielded VMs for Linux.” This approach makes it easier and more straightforward to use Linux with Windows.
  • Microsoft Defender Advanced Threat Protection: Cybersecurity is a major concern for businesses, particularly considering advanced persistent threats. These attacks can get through many antivirus software solutions by using social media profiling, whaling, and spear phishing as ways to gain entry to the network.
    This makes having an advanced threat protection (ATP) system essential for protecting systems and data. Microsoft understood this need when they released Microsoft Defender ATP as part of Windows Server 2019.
    Microsoft ATP does more than monitor accounts for suspicious activity. It tracks the activities of users, prevents unauthorized changes to log files, and automatically investigates attacks. It also provides options for remediation.
  • Leaner Server Core: Microsoft introduced Server Core in 2008 as a minimal installation option for Windows Server. With the 2019 release, Server Core is now even smaller, down to 50% the size of Windows Server 2019, with the full GUI features.
    The reduction in size extends to the use of container delivery to provide software to user-owned devices. While reducing overhead, container delivery maintains the necessary security for the software.
  • GUI interface: The Windows Server 2019 release includes all the administration tools in a full GUI front end. This is not, however, available for use with Server Core or Nano Server.

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Specialized Editions of Windows Server

Long-Term Servicing Channel

Some companies find it difficult to upgrade each time a new version of Windows Server is released. To support those companies, Windows Server is part of Microsoft Long-Term Servicing Channel (LTSC), formerly known as the Long-Term Servicing Branch (LTSB).

Products in LTSC remain supported for a full ten years. This covers five years of support as part of the purchase, and another five years with a support contract extension. When a new version comes out, companies with the prior version of Windows Server don’t have to automatically upgrade.

When businesses do upgrade, though, their existing license doesn’t cover the new version, so they’ll need to purchase it separately. The R2 versions are the exception, since those are supplied as a free upgrade to customers who have the original version of the release. For example, upgrading to Windows 2008 R2 was free for customers who had Windows Server 2008.

Several versions of Windows Server are still in active use today: 2008 R2, 2012 R2, 2016, and 2019. If you’re wondering, “What version of Windows server do I have?” you can find out by going to the About section in the System area of Settings.

Semi-Annual Channel

Not all companies need or want to wait ten years to upgrade. For companies needing more frequent updates and innovations, Microsoft introduced another purchasing model, the Semi-Annual Channel (SAC), in 2017. SAC Windows Server products have new releases every six months, with support contracts that only last eighteen months.

The products in this channel aren’t the same as the products in LTSC, which means they’re not interchangeable. Customers wouldn’t be able to upgrade from Windows Server 2016 to an SAC version, or vice versa.

Another difference is while the LTSC editions use the standard Windows naming convention, the SAC editions are named based on the year and month of the release. So far, the following SAC Windows Server versions have been released:

  • Version 1709 (September 2017)
  • Version 1803 (March 2018)
  • Version 1809 (September 2018)
  • Version 1903 (March 2019)
  • Version 1909 (September 2019)

As well as being released more often, these SAC versions don’t have as many user interface features as the LTSC Windows Server editions. The SAC versions are also integrated into Microsoft subscription servers in the cloud, including Azure Marketplace, Visual Studio, and Software Assurance.

Windows Server Cloud

Using Windows Server in the cloud frees up companies from the need to host the software on their on-premises machines. Instead, they can use a remote infrastructure such as Microsoft Azure cloud servers, offered on a subscription basis. You can also use other cloud providers, such as Google Cloud, for Windows Server. Having third-party options gives you more flexibility in choosing which plan works best for your company.

For companies wanting a hybrid approach, where only some of the server activity is in the cloud, this is also supported with the latest versions of Windows Server. Whatever approach you take will give you seamless service.

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Best Windows Server Monitoring Software

Microsoft provides some monitoring functions as part of Windows Server, but to fully manage the system, you’ll need additional monitoring software. This is necessary to track any problems with the hardware and to ensure all the server connections are operating correctly. This is true for both the cloud and on-premises versions of the system.

SolarWinds Server & Application Monitor (SAM) is an invaluable tool to assist you with monitoring Windows Server. It allows you to:

  • Customize alerts to notify you about metrics such as network load balancing
  • Monitor Windows performance and third-party applications like Oracle and Apache
  • Optimize the utilization of resources and forecast the need for future capacity
  • Perform an inventory of networked assets and identify any failures on server hardware


With SAM implemented, you won’t have to spend time on manual checks or wait for things to finish due to slow performance. The automated processes allow you to spend your time on other tasks without worrying about missing a problem area.

This is just one of the tools in the SolarWinds suite of Microsoft monitoring and management tools. These infrastructure tools run on a common platform called the Orion® Platform and support the range of Microsoft technologies. This covers Windows Server, as well as Hyper-V, Azure, Office 365, and more.

Since these tools are on a shared platform, you can easily use one or more of them together. You also have access to options like the PerfStack dashboard, a multi-module utility that looks not only at Windows Server but also at the support services and hardware. If any element is running poorly and is causing performance degradation, PerfStack enables you to identify the problem area, so you can address it early on.

You can try SolarWinds SAM and other Microsoft management tools with a 30-day free trial.

Implementing Windows Server

Microsoft knows not everyone has the same needs for their operating systems, which is why they have different options for Windows server versions. Some businesses don’t have the capacity to upgrade to every new version, and some may not want to upgrade because new releases aren’t always stable. Other companies may need more frequent updates and the latest enhancements.

For companies wanting longstanding functionality, the Long-Term Servicing Channel is a good option. Those who prefer regular updates should look at the Semi-Annual Channel or go with a subscription-based cloud approach to keep their operating system up to date.

Whichever option you choose, make sure you also have a good tool to monitor Windows Server, such as SolarWinds Server & Application Monitor. This will allow you to make the best use of your operating system. It will also give you peace of mind in knowing you don’t have to worry about undiagnosed problems.

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