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Windows Server Buyer's Guide

What is Windows Server? Windows Server is a server operating system from Microsoft. It is different from a UNIX-based operating system in that it offers easier management through a better interface. The Windows Server web hosting environment supports major web programming languages and databases like PHP, MySQL, ASP.NET and MS SQL. There are a lot of advantages to the Windows Server.

If you are familiar with Windows, getting used to Windows Server is easy. Most of the people using Windows Server hosting use ASP.NET, which is a free web framework for building web sites and web applications using HTML, CSS, and JavaScript. Those who use it can develop websites using the familiar interface of Microsoft tools such as Web Deploy and Visual Studio. With ASP.NET, users can also develop a database-driven website with Microsoft SQL database. Another advantage is that Windows Server can run PHP and MySQL, which are common and popular programming and database options. Overall, the versatility of the Windows Server makes it attractive.

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How to Choose the Right Version of Windows Server?

How do you choose the right Windows Server for you? Do you need Windows Server 2008 R2, Windows Server 12 R2, or Windows Server 2016, are do you need Windows Server 2019? Are there differences, is one more powerful, what are the features, does it it depend on the size of your business? Let’s look at some of the things to consider before you make a buying decision.

What Are Roles and Features in Windows Server?

There are differences between roles and features. A server role is a set of programs that can be installed and configured to let a computer perform a specific function for multiple users or other computers on a network. Roles describe the primary function, purpose, or use of a computer. A single computer can be dedicated to perform a single role heavily used in the enterprise, or it can perform multiple roles. Roles also provide users throughout a company access to resources managed by other computers, such as websites, printers, or files stored on different computers. Roles also usually have their own database for handling user requests. Once installed, roles allow users to perform the specified tasks with limited supervision or outside input. Features are add ons that support or augment the functionality of one or more roles, or improve the functionality of the server.

Here are some server roles:

  • Windows AD/DC Server
  • DNS
  • DHCP
  • File
  • Print
  • NAP
  • Terminal Server
  • IIS
  • WDS
  • WSS

Here are some features

  • .NET
  • Bitlocker Encryption
  • BITS
  • Remote Assistance
  • SMTP Server
  • SNMP
  • Telnet server & client
  • Failover
  • NLB
  • TFTP
  • Windows Server Backup
  • WINS
  • Powershell

Understanding the differences between roles and features is an essential part of determining which Windows Server is right for you.

Versions of Windows Server

There many versions of Windows Server. There is Windows Server 2008, Windows Server 2012, Windows Server 2016, and Windows Server 2019. In addition to these versions, there various editions of Windows Server. One of factors that you might use when choosing the WIndows Server for you is budget. How much of a budget does your company have? Older versions of Windows Server are more affordable and more accessible to companies with limited budgets, but when you use older versions, Microsoft may no longer offer mainstream support. What does this mean for your company? Depending on your needs, maybe it’s a viable solution, or at least a workable solution until you can expand your budget. Maybe it isn’t even budget. Maybe your hardware isn’t advanced. This is another reason you may not want to use a newer version of Windows Server. Here are some of the best Older Versions Windows Server for small business:

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Windows Server 2008 R2

Developed from the foundation of Windows Server 2008, the Windows Server 2008 R2 Standard edition offers more reliability flexibility than the previous version. Small businesses are able to rely on this server to provide services like DNS, print, remote access, domain, web, and application. There are some great new functions her as well that can assist in ensuring power savings, virtualization, and manageability. Top line remote desktop services make telecommuting and field work easy to manage and more consistent. For now, Windows Server 2008 is available from trusted resellers like

Windows Server 2012 Foundation

This version is built to support x64 socket, making it ideal for small business. With 2012 Foundation, you can integrate and operate the most ideal and fitting business applications with the most important features. These include sharing files, strong security, and remote access. This is limited to 15 users only, so it’s ideal for companies with less employees than that. It’s an affordable and functional way to get the power of Windows Server in your small business.

Windows Server 2008 Enterprise

This is a step up and still great for small business. This is particularly great for small businesses that depend on technology and digital processes. Windows Server 2008 Enterprise brings you the range and scalability needed to use it for your small business and to keep up with you as your business grows. Much has been said about the superb integration of up to date security settings and its outstanding uptime level. Includes cost-effective methods for maximizing virtualization. Top-tier applications like messaging systems, print and file, services, and databases are given higher accessibility. This version allows unrestricted numbers of Virtual Private Network connections, making it flexible, cost-friendly, and ready to grow right along with your business.

Windows Server 2016 Essentials

This one is for a small business with minimal IT requirements. It has all the basic features for running a small business effectively, efficiently, and on a budget. Windows Server 2016 Essentials can be accessed and used by up to 25 users and 50 devices.

These are cost-effective suggestions for small business with a limited budget, limited functionality needs, or both. What about more current versions? This is a range of editions that will cover the needs of small to large businesses.

Windows Server 2016

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Windows Server 2016 is available in 3 editions. The Foundation edition, like it was offered in Windows Server 2012, is no longer available for Windows Server 2016.


Is ideal for small businesses with basic IT requirements. This means a company that is very small and has no IT department or even a dedicated IT specialist can benefit from the features and capabilities of this edition. CALs are not required for Essentials, but it is limited to 25 users/50 devices.


This edition of Windows Server 2016 is for mid to large size companies that need advanced features and virtualize to a lesser extent. This is really one of the most popular editions for a range of businesses. Standard allows for two virtual machines and requires CALs.


Is the workhorse for companies of any size that have high IT requirements and huge IT workloads utilizing many virtual systems. Datacenter allows for unlimited virtual machines and requires CALs.

Windows Server 2019 is brand new and brings much more functionality to the table. Since the range of potential deployments makes impossible to pinpoint any realistic recommended system requirements, you need to always consult specific product documentation for each of the server roles to determine what you need to deploy the way you want to deploy. If you have the budget, Windows Server 2019 is a powerful choice, with all of the expected editions to offer you the widest range of productivity.

When is Windows Server Out of Date?

Although Windows Server 2008 is still used in many businesses, you might ask when your WIndows Server is out of date. The truth is, if it still effectively does what you need it to do, your Windows Server is still good. Keep in mind, however, that mainstream support falls away, and has fallen away for most older versions of WIndows Server. That means less security and no updates, which can bad for business.

If you want to get more features and not have to expand your budget much, Windows Server 2012 is a great alternative. There are four editions of Windows Server 2012 to choose one, with each offering different features and functionality to suit whatever size business and budget you need. They are:


Is the edition you don’t have access to in Windows Server 2008, so that’s a plus for you. Foundation is designed to give you extreme cost effectiveness and is ideal for the small budgeted business. It’s a basic starter edition of Windows Server 2012, making it ideal for a small business without an IT department or dedicated IT employees. You get all the essential server functionality without virtualization rights. Server licensed and limited to 15 users.


Nearly the same as Foundation, with a bit more functionality and the ability to have up to 25 users. There is still no virtualization rights. Essentials is ideal for small companies with a bit more budget and maybe an IT employee or two.


This is great for non-virtualized or lightly virtualized environments. Small to mid companies can benefit here, especially with an IT department, no matter how big or small. Includes all features with two virtual instances. Licensing is processor plus CALs.

These editions are also available for Windows Server 2019.

Is Migrating to Another Version of Windows Server a Good Idea?

A lot of companies and organizations wonder if migrating to Windows 2016 or to the new 2019 is a good idea. There are a lot of reasons to switch, but factor in the cost. If you’re still using a fairly outdated operating system and computers, moving over to Windows Server 2019, or even 2016, might not even be an option. If your business has started to use cloud services like Microsoft Azure, Windows Server 2019 certainly bring offers enough new functionality and reasons to migrate. Here are some reasons.

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  • Cloud-ready application platform
  • Added layers of security for better piece of mind
  • Software-defined data centers
  • Affordable enterprise ready Azure-inspired infrastructure
  • Privileged identity protection
  • Breach resistance Secure virtualisation
  • Built-in SDDC capabilities
  • Traditional and cloud-native applications
  • Containers/microservices Azure hybrid use benefit

The enhanced security updates alone make Windows Server 2019 or even Windows Server 2016 reason enough to upgrade. In the end, it will all depend on your budget, the hardware you’re running, and understanding the needs of your company versus what you can get from Windows Server, whether you are looking at staying with an old version or looking to move up to something more current with better features and more security.

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