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This guide is a combination of TechSoup US’ Guide to Windows Server Editions and Chloe Green’s  “A guide to Windows server editions - which one is right for your charity?” (Tech Trust). This content has been adapted by TechSoup Canada for a Canadian audience.

Getting started

It can be tricky to determine which edition of Microsoft Windows Server is best for your nonprofit. Each organization has different wants and needs, so the server selection process isn’t black and white.

To help you make an informed decision, we’ve drawn up a quick guide to summarize the benefits you get with each edition of Windows Server.

Key terms


A server is a “computer designed to process requests and deliver data to another computer over the Internet or a local network” (Lifewire). The term “server” generally refers to the physical hardware system, and “server software” is the program that performs a specific task (i.e. pushing and pulling data from a network). Depending on the size of the computer network, both in terms of how many users are connected to the network (e.g., staff, volunteers, etc.) and/or the amount of data the server is moving (e.g., database of 30,000 records vs 300,000 records), more servers may be needed to ensure the network can function as intended.

Client Access License

Some server software require a license for each user or device that will access the server. These licenses are call Client Access Licenses or CALs.

Types of server licenses

Core-based licenses are required for each execution core contained in the same integrated circuit within a computer’s central processing unit, whether cores are virtual or physical.

CPU-based or Processor-based licenses are required for each server on which Windows Server will be installed. Each CPU-based license can only be used on a single server with a maximum of two physical processors.

Choosing your Windows Server software

Essentials edition

This server software has a built-in integration with Office 365 hosted services making it ideal if you are anticipating a move to the cloud. Solutions are also included for quick and easy remote computer and file access. Additionally, you don’t have to buy individual user or device CALs and the upfront cost is the entirety of what you have to pay.

  • Organization size:
    Best for a small nonprofit that doesn’t anticipate growth in the short-term: the reason being the maximum users/devices that can access the server (see limitations, below).

  • License:
    CPU-based (does not require or allow CALs). The licensing process for Essentials is straightforward and doesn’t require any additional purchases. This also makes the installation process pretty easy too.

  • Limitations:
    With this edition you are limited to 25 users or 50 devices. This means, if your organization is planning to grow in size in the next 2-5 years, you may find yourself needing to make a switch further down the line. Thankfully, offers available through TechSoup Canada should keep the costs to a minimum!

Standard Edition

Standard edition is an ideal middle ground between Essentials (above) and Datacenter (below) as it offers a lot of the benefits of the latter at a more budget-friendly cost. These factors make it an ideal fit for small to medium-sized organizations. The Standard edition offers users capability to run 2 virtual machines (also called Hyper-V containers; see article from Lifewire). Additionally, Windows Server Standard also offers fully integrated services and direct access for users.

  • Organization size:
    Suited to small-to-medium organizations that don’t need to run numerous virtual machines.

  • License:
    Core-based (requires CALs). The licensing process for this edition (as well as Datacenter, below) can be a bit tricky. The purchase must be of at least 16 core licenses per server (core licenses are sold in 2-packs). If the server has more than 16 cores, the number of core licenses purchased must equal the number of physical cores on the server.

  • Limitations:
    Two virtualized environments will be enough for most nonprofits. Nonetheless, if you think your demands may increase over time, you could incur greater costs than if you had chosen to go with Datacenter from the outset, which allows multiple Hyper-V containers.

Datacenter Edition

If the technical specs of the Standard Edition suits your needs, but you need to run more than 2 virtual machines, then Windows Server Datacenter edition would the best solution. With Datacenter edition, your device can efficiently while performing multiple demands.

  • Organization size:
    Medium to large or with extensive IT demands.

  • License:
    Core-based (requires CALs). The licensing process is the same as that for the Standard edition (see above).

  • Limitations:
    The biggest limitation that many find with Datacenter is the cost. At full price it is around 8 times the price of Windows Standard server. Luckily, eligible nonprofits can minimize this limitation by requesting it through TechSoup Canada, but it still remains the more expensive of the two. It’s important to assess what demands you have for your technology before making a purchase. Additionally, think about what demands you predict for the near future.

Client Access Licenses and External Connector Licenses

Windows Server Standard and Datacenter editions require a Windows Server user or device CAL for each user or device accessing or using the server software. No CALs are needed for the Essentials edition, which means Essential edition’s maximum of 25 users and 50 devices can't be exceeded.

Alternatively, an organization can use a Windows Server external connector licenses (ECL) for a large number of authenticated external Internet users. An external user is a person who is not an employee or someone to whom you provide hosted services using the server software. No CALs are needed for anonymous Internet users, such as unidentified users browsing the organization's public website.

CALs and ECLs offered through TechSoup Canada are always for the currently offered version of the server software. However, these licenses can also be used with earlier versions of the server software.

Remote Desktop Services

If the server is running Remote Desktop Services (previously known as Terminal Services), separate Remote Desktop Services CALs or ECLs are required to access the services. Remote Desktop Services allows the remote execution of applications from a wide range of devices over virtually any type of network connection.

Rights Management Services

If the server is running Rights Management Services (RMS), separate RMS CALs or ECLs are required to access the services. RMS is information-protection technology that works with RMS-enabled applications to help safeguard digital information from unauthorized use. RMS functionality is included in the Windows Server license.

RMS licensing is not available through TechSoup Canada.

Server Application Licenses

Licenses for server applications — such as SQL Server or Exchange Server — that run on the Windows Server platform are separate. General licensing requirements for server applications offered through TechSoup Canada can be found in the product descriptions.


If you have earlier versions of Windows Server with active Software Assurance, you can upgrade to Windows Server 2016 without placing a new donation request. Since Windows Server 2016 has changed to a core-based licensing model, organizations with Software Assurance will be granted a certain number of core licenses, depending on how many processor licenses they have. See the Windows Server 2016 licensing datasheet (PDF) for details.

For help upgrading, see Windows Server installation and upgrade information in the Windows Server TechNet Library.

CALs, ECLs, and management licenses (MLs) work if they are for a version equal to or earlier than their server software. However, if you upgrade to Windows Server 2016, you will also need to use Software Assurance to upgrade your CALs.


Downgrade rights allow you to obtain Windows Server in any version that Microsoft continues to make available for download through the Volume Licensing Service Center. With Windows Server, you can choose to download the 2016, 2012 R2, or 2012 versions of the edition you've licensed. Downgrading does not depend on Software Assurance; it is a benefit of Volume Licensing.

However, with the release of Windows Server 2016, all previous versions of Windows Server have been transitioned to the new core-based licensing model. If you are planning on requesting new or additional licenses for a previous version of Windows Server, make sure you get enough licenses to cover all the cores on your licensed server according to Windows Server 2016 licensing guidelines. See the Windows Server 2016 licensing datasheet (PDF) for details.

CALs obtained through TechSoup Canada will work with the downgraded version.

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