Convert Windows Server Essentials or Evaluation to Retail Edition

Microsoft encourages everyone to explore the features of the server platform by utilizing trial versions of Windows Server (Standard Evaluation or Datacenter Evaluation). Upon installing Windows Server Evaluation, you have 180 days to assess its capabilities. This period allows you to access the full functionality of Windows Server. In this article, we shall discuss how to Convert Windows ServerEssentials or Evaluation to retail edition. Please see All About Windows Server 2016, “MSSQL Server evaluation period has expired: How to upgrade SQL Server instance“, and how to enable Amazon S3 default bucket encryption using S3 Console.

Note: Before proceeding in details, I will let you know that these since Windows Server Data Centre Edition is a retails Edition, therefore, it cannot be upgraded.

So, we can upgrade Windows Server Evaluation Edition and Windows Sever Essential Editions which have been discontinued. But in this article, we will focus on converting our Windows Sever Essenial Edition.

See how to check Windows Activation Status and troubleshoot activation errors, and how to check Windows 10 activation status and change the product key.

What are the Differences between Windows Sever Evaluation, Essential and Retail Edition?

Microsoft offers an integrated server suite known as Windows Server Essentials for businesses with no more than 25 users or 50 devices. As of Windows Server Essentials 2022, OEM providers exclusively provide this product.

The licensing terms and restrictions concerning the number of users/devices and cores remain unchanged. Additionally, Windows Server Essentials 2022 provides the same features as Windows Server Standard 2022.

Windows Server Evaluation Edition is a trial version of Windows Server designed for testing and evaluation purposes. It comes with a limited evaluation period (usually 180 days), after which the system will start shutting down regularly if not activated.

It includes all the features available in the full retail edition of Windows Server. During the evaluation period, you’re encouraged to activate and convert it to a full retail version to continue using it without interruptions.

This can be converted to Standard and Datacenter Edition

The Windows Server Retail Edition is the full commercial version of Windows Server intended for production use. In order to use it beyond the trial period or without limitations, you need to purchase a license key and activate the product.

The Retail editions come with full Microsoft support and are eligible for updates and patches. Organizations acquire licenses based on the number of users or devices accessing the server.

Convert Windows Server 2019 Essential Edition to Standard Edition

This step can be applied to Windows Server Evaluation Edition. By, I have to show you this with an Essential Edition as this is what I currently have in my lab.

Note: Since Windows Server Essentials have been deprecated. Microsoft highly recommend Microsoft 365 for small business customers as a replacement for all versions of Windows Server Essentials.

The most important difference between these 2 is that Windows Server 2022 Essentials is usable up to 25 users and 50 devices, whereas Standard does not have such a limit. A consequence of this, is that Windows Server 2022 Essentials does not require user/device CALs, but Standard does require these CALs

Please see how to Transfer Windows License from one PC to the other on Windows, How to find your Windows 10 Product key, and How to upgrade Windows Server Evaluation to Full Version.

Convert Windows Server Essential Edition to retail edition

Launch PowerShell with Admin rights.

To get the available editions:

DISM /Online /Get-TargetEditions

Please see How to deploy Folder Redirection in Windows, and Sign-in options for Windows: Ditch Password for Enhanced Security.

To set your Windows Server to a higher edition

You can use the same steps to convert to Datacenter Editions and also apply them to Windows Server Evaluation Edition.

Now, let’s set this Essential Server to Windows Standard Edition by using the command below. Kindly do not forget to replace it wit your product key.

DISM /online /Set-Edition:ServerStandard /ProductKey:XXXXX-XXXXX-XXXXX-XXXXX-XXXXX /AcceptEula

Note 1: From Eval to Datacenter, use this command below.

DISM /Online /Set-Edition:ServerDatacenter /ProductKey:xxxxx-xxxxx-xxxxx-xxxxx-xxxxx /AcceptEula

You can observe that this step will require a considerable amount of time and involve multiple restarts. Additionally, it’s worth noting that the server edition has undergone a change

Note: You can simply activate Windows over the activation window as shown below. Since we have a lot of articles on this, I will be showing you how to Manage Windows Product key with Software Licensing Manager.

The below error “Can’t activate Windows on this device as we can’t connect to your organization’s activation server” has been discussed already. But I will show you he steps here also.

Activate Windows

You will also notice that Windows has not been activated yet. 

Now, re-enter the keys. To do this, please follow the steps discussed below.

Step 3 – Install KMS client key

Replace your_license_key with following volumn license keys according to Windows Edition:

slmgr /ipk your_license_key

Step 4 – Set KMS machine address

Replace kms_server with the real KMS server address.

slmgr /skms kms_server

Step 5 – Activate your Windows

Let’s activate Windows

slmgr /ato

Successfully converted the Windows Server 2019 Essential image to Windows Server 2019.

Below is an image showing the conversion of Windows Server 2022 Evaluation Edition to Windows Server 2022 Data Center Edition.

I hope you found this article useful on how to Convert Windows ServerEssentials or Evaluation to retail edition. Please feel free to leave a comment below.