Windows Server

How-to: Upgrade Windows Server 2016 to Windows Server 2019/2022 | Best Practices

Windows Server 2016 is reaching the end of its extended support window in 2027. Upgrading to a newer version, like Windows Server 2019/2022, ensures continued security updates, bug fixes, and improved performance. This guide outlines the best practices for navigating the upgrade process, offering both in-place and fresh installation options.

Choosing the Right Path to Windows Server 2016:

  • In-place Upgrade: Fast and convenient, preserves settings and data (limited to two versions at a time). Requires compatibility checks and poses potential risks.
  • Fresh Installation: Offers a clean slate and greater flexibility, but necessitates manual data and application migration. More time-consuming and requires downtime.

Best Practices for Both Options:

1. Compatibility Checks:

  • Hardware: Ensure your hardware meets the system requirements for your chosen upgrade path. Refer to Microsoft’s official documentation for details.
  • Software: Verify compatibility of your applications and third-party software with the newer version. Consult vendor websites or perform test installations.

2. Backups & Snapshots:

  • Create complete backups of your entire system, data, and applications before proceeding. Consider cloud-based or offsite backup solutions for added security.
  • For virtual machines, create snapshots in case of rollback needs.

3. Thorough Planning & Documentation:

  • Plan the upgrade process meticulously, considering downtime impact, rollback procedures, and post-upgrade configuration changes.
  • Document every step, including compatibility checks, chosen upgrade path, specific commands, and potential roadblocks encountered.

4. Test Environments:

  • If possible, set up a test environment to simulate the upgrade process and identify potential issues before proceeding on your production server.

5. Upgrade During Off-Peak Hours:

  • Minimize disruption by scheduling the upgrade during off-peak hours or low-traffic periods. Notify affected users beforehand.

6. Post-Upgrade Monitoring:

  • Closely monitor your server’s performance, resource usage, and event logs after the upgrade to identify any unexpected issues.

In-place Upgrade Step by Step to 2019

How-to: Upgrade Windows Server 2016 to Windows Server 2019/2022 | Best Practices | System Properties on your server 2016
  • Before start installation check current windows version
  • Locate the Windows Server 2019 setup media, run setup.exe directly.
  • Select Download updates, drives and optional features (recommended) and click Next.
  • Setup checks your device configuration, you must wait for it to finish, and then select Next.
  • Select the version of Windows Server 2019 you want to install and click Next.
  • the license agreements often appear different. Click Accept
  • Accept the terms and then select Keep personal files and apps to choose to do an in-place upgrade, and then select Next.
  • After Setup analyzes your device, it will prompt you to proceed with your upgrade by selecting Install.
  • Then upgrade Windows Server 2016 to 2019 for will begin. After the upgrade is complete, your server will restart.


Upgrading Windows Server 2016 requires careful planning and execution. By following these best practices, you can minimize risks and ensure a smooth transition to a more secure, performant, and feature-rich server environment. Remember, the chosen path (in-place or fresh installation) depends on your specific needs and resources. Weigh the pros and cons of each option carefully before making a decision. For additional resources and detailed instructions, refer to Microsoft’s official documentation linked within this guide.

Helpful Resources:

I hope this information helps you decide on the best approach for upgrading from Windows Server 2016.

Leave a Reply

Your email address will not be published. Required fields are marked *

Back to top button
TOC ......