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To buy Windows Server Licensing without spending more than necessary can be tricky. The adage is, if you think you need a CAL you probably do. But that is not always the case. One thing that is for certain is that failing to prepare for server migration is preparing to overpay for server licensing. Here are a few things that will cost a company more than it should when it comes to administrating assets on Windows Server software.

1. They fail to update on time

Windows Server 2003 users that take an “ain’t broke, don’t fix” approach to end of service place their business in a risky situation. It is a costly one too—CALs will increase in price by 13 percent come August 1. Also, if you think getting current with Windows Server is expensive, compare it to the costs of downtime that results from a server-related system outage or regulatory compliance violation. Updating should be a no-brainer. If that doesn’t seem as such, read: Microsoft Server 2003 End of Life: 5 Silver Linings

2. They buy Device CALs when they should buy User CALs

And vice versa. A Device CAL covers every device that accesses a Windows Server environment regardless of the number of users that use it for access. A User CAL covers Windows Server access on a per user basis—whether for file sharing, printing, Active Directory, or any other capacity that utilizes Server assets. Which CALs make the most sense depends on your environment. Will you have more devices, or more users accessing your servers? Make sure to take inventory before deciding which route to take.

3. They forget to account for growth

The three tiers of Windows Server 2016 cater to specific user-counts and their computing needs. However, the licensing is not designed for easy scalability between each tier. That said, planning ahead for future growth will save on future expenditures. To illustrate, Windows Server Essentials provides support for up to 25 users and 50 devices without requiring CALs—a great option for a SMB under 25 seats.  But once that SMB grows past that user limit they essentially have to go through the entire migration process over again to upgrade to Windows Server Standard. That is no good.

Likewise, a company that uses Windows Server Standard should take into consideration whether they will increase virtualization in the years ahead. If there is a chance that Standard’s two virtual machine limit might be surpassed, perhaps consider Windows Server Datacenter which provides support for unlimited VMs.

Note that Microsoft charges per server core for licensing Windows Server hardware.  That means if you upgrade server hardware and are working with more cores in your servers, you may need to purchase Windows Server 2016 additional core licensing.

4. They license virtual machines and administrators

License users and hardware, but not the VMs. That is the hard and fast rule if you virtualize instances of Windows Server. Again, with Standard there is a maximum to two virtualized instances; with Datacenter you can run unlimited VMs without needing CALs, if the software is used solely to:

  • run hardware virtualization software
  • provide hardware virtualization services, or,
  • run software to manage service operating system environments on the licensed server.

In many situations this essentially frees system administrators from the CAL requirement. Note that if administrators use the server network for any other purposes, a user CAL is needed. SourceLicensing brief: Licensing for virtualization technologies (Dec. 2017, PDF download).

5. They license a web server

Server-to-server communication tends to not require CALs. It follows, then, that Windows Servers configured to run a Web Workload do not require CALs either. Microsoft defines a Web Workload server as “publicly accessible and consist solely of web pages, web applications, web services and POP3 mail serving.” This definition covers most web server situations, which likely fall under the auspices of different server licensing such as Windows Web Server or SQL Server. Source: Microsoft Licensing Blog

6. They license Windows Server instances in Microsoft Azure

No CALs are required for accessing Server instances running in the Azure environment, as access rights are included in Azure’s per-minute charge. Source: Microsoft’s Virtual Machines Licensing FAQ page.


Make sure to take note of these items, but understand that preparation is the key for saving money. Take advantage of everything that is available. There are several great free resources that help with planning out a migration from Windows Server 2008 and licensing needs before you buy Windows Server licensing.

Need help with Windows Server licensing? Contact our Windows licensing specialists at [email protected]  or call (888) 482-66778.

Why Companies Overpay for Windows Server Licensing
Article Name
Why Companies Overpay for Windows Server Licensing
To buy Windows Server Licensing without spending more than necessary can be tricky. The adage is, if you think you need a CAL you probably do. That is not always the case.
Adam Lovinus

Author Adam Lovinus

A tech writer and Raspberry Pi enthusiast from Orange County, California.

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