How to Upgrade to Windows Server 2025: An Overview of All Options for Your Situation

Upgrading your Windows Server environment provides your business with newer features and enhanced security. Additionally, you need to meet increasingly strict requirements for business software and compliance. Since technology is constantly evolving, it is essential to update your server system regularly. Depending on the version you are currently using, different upgrade options are available. In this blog, we provide an overview to help you plan the right upgrade from Windows Server 2012 to Windows Server 2025.


Windows Server 2012

For businesses using Windows Server 2012, upgrading to a newer version is a crucial step in improving security and performance. Direct upgrades to later versions such as Windows Server 2019 or 2022 are not supported. The upgrade path for Windows Server 2012 is limited to an upgrade to Windows Server 2012 R2 or Windows Server 2016. Businesses still running Windows Server 2012 must first upgrade to the intermediate version (2012 R2) or directly to 2016 before they can proceed to newer versions. This is essential to prevent compatibility issues and ensure the stability of the server environment.

Windows Server 2012 R2

Businesses using Windows Server 2012 R2 have multiple upgrade options. You can upgrade directly to Windows Server 2016, Windows Server 2019, or even Windows Server 2025. This provides greater flexibility for organizations using Windows Server 2012 R2, allowing them to choose an upgrade path that best suits their business and budget. The choice between versions 2016, 2019, and 2025 depends on the features available in later versions, security requirements, and integration possibilities.


Windows Server 2016

If your company is currently using Windows Server 2016, you can upgrade directly to Windows Server 2019, Windows Server 2022, or Windows Server 2025. Windows Server 2016 provides a strong foundation for many organizations, but the latest versions of Windows Server include improvements in cloud integration, virtualization, and security. Upgrading to a newer version gives you access to innovative features such as hybrid cloud capabilities, enhanced management options, and security features. An example of these security features is the improved Windows Defender.

Windows Server 2019

Users of Windows Server 2019 can easily upgrade to Windows Server 2022 or Windows Server 2025. This makes the transition to a newer platform seamless, without sacrificing stability and performance. Since Windows Server 2019 is still widely used, extensive documentation and support channels are available for this version. Organizations upgrading to Windows Server 2022 or 2025 will experience many improvements in application compatibility, network security, and cloud-native technologies.

Windows Server 2022

With Windows Server 2022, the transition to Windows Server 2025 is also straightforward and recommended for organizations ready for the latest technologies. Windows Server 2022 offers high-quality features such as stricter security measures, improved performance, and broader support for cloud and hybrid environments. For organizations investing in long-term technology, upgrading to Windows Server 2025 is a future-proof choice. It provides features fully optimized for modern cloud-based infrastructures.

If you're interested in our Pre-Owned Windows Server licenses, request a quote. Contact us and discover how much you can save on Windows Server licenses. In addition to Windows Server 2025 licenses, Softtrader also offers previous versions. If your company wants to invest less, these earlier versions are a great alternative.


Important Considerations When Upgrading

When planning your upgrade to a newer version of Windows Server, there are several key considerations to ensure a smooth transition:

  1. Compatibility
     Ensure that your hardware and applications are compatible with the target version of Windows Server. Check vendor documentation for specific requirements, especially if you use specialized software or custom systems. Not all older systems support the latest versions of Windows Server, so hardware upgrades may be necessary.
  2. Backups
     Always create full backups of your systems before performing an upgrade. This minimizes the risk of data loss in case of unexpected issues and ensures that you can revert to a previous system version if technical complications arise.
  3. Licensing
     Verify that your current licenses are valid for the version you plan to upgrade to. Windows Server licenses are often version-specific, meaning additional licensing requirements or costs may be associated with upgrading to a newer version. It's important to budget for these costs, as license prices vary depending on the version and infrastructure used (e.g., Standard or Datacenter editions).
  4. Test Environment
     Perform the upgrade in a test environment first to identify and resolve any issues before updating the production environment. This helps ensure a smooth upgrade and prevents unexpected disruptions that could impact business operations.
  5. Security & Compliance
     Upgrading to a newer version of Windows Server grants access to the latest security updates and features. This is crucial as cyber threats are becoming more advanced. An upgrade can help protect your systems from vulnerabilities that may exist in older versions.
  6. Support & Updates
     Newer versions of Windows Server receive regular updates and long-term support from Microsoft. Using outdated versions may eventually result in no longer receiving security patches, leaving your network vulnerable to cyberattacks.

Interested in Upgrading Your Windows Server?

Upgrading your Windows Server environment provides your organization with improved performance, enhanced security, and new functionalities. By choosing the right upgrade path based on your current version, you can prepare your organization for the future. It's important to plan each step carefully, considering compatibility, licensing, security, and backups. With the right preparation, you can ensure a seamless transition and fully leverage the potential of the latest Windows Server versions.

If you're interested in Windows Server licenses, request a quote or contact us. With Softtrader, you can save up to 70% on Microsoft licenses. We are ready to provide you with information on the different upgrade options. Save on your Windows Server licenses with Softtrader!