Windows Server 2016 direct upgrade to Windows Server 2025

Upgrading directly from Windows Server 2016 to Windows Server 2025 is supported, but the success rate depends heavily on system health and the upgrade path used. The commands you’re already running (sfc, DISM cleanup, and restorehealth) are the right baseline checks. Beyond that, the most important preparation steps are ensuring all cumulative updates are applied on the 2016 system, removing any legacy or third‑party filter drivers (especially antivirus or backup agents), and confirming that the VM configuration in GCP matches supported virtual hardware for Server 2025. Microsoft’s guidance also stresses not attempting in‑place upgrades on Domain Controllers, and verifying application compatibility before proceeding. If you continue to see failures, it’s often due to outdated drivers or unsupported GCP guest agent versions, so make sure the GCP upgrade script is the latest release and that the VM has the current Google guest environment installed.

You can refer to this article: https://techcommunity.microsoft.com/blog/windowsservernewsandbestpractices/upgrading-to-windows-server-2025-from-windows-server-2012-r2-2016-2019-or-2022-u/4456406?utm_source=copilot.com

To prepare for a direct upgrade from Windows Server 2016 to Windows Server 2025, you are already taking important steps by running commands like sfc /scannow and dism commands to ensure the integrity of your system files and clean up the component store. Here are additional recommendations to enhance your chances of a successful upgrade:

1. Backup Your Data: Always ensure you have a complete backup of your system and important data before proceeding with any upgrade.
2. Check for Updates: Ensure that your current Windows Server 2016 installation is fully updated with the latest patches and updates from Microsoft. This includes installing any cumulative updates.
3. Remove Unnecessary Software: Uninstall any applications or services that are not needed, as they may interfere with the upgrade process.
4. Disable Antivirus Software: Temporarily disable any antivirus or security software that might block the upgrade process.
5. Check Disk Space: Ensure that there is sufficient disk space available on the system drive to accommodate the upgrade.
6. Review Logs: Check the Windows Event Viewer for any warnings or errors that might indicate underlying issues that could affect the upgrade.
7. Use Upgrade Assessment Tools: Consider using tools like the Azure Virtual Machine (VM) Windows OS Upgrade Assessment Tool to validate the OS upgrade path and identify any known issues.
8. Verify Compatibility: Ensure that all hardware and software components are compatible with Windows Server 2025.

Following these steps can help mitigate potential issues during the upgrade process. If problems persist, consider consulting Microsoft documentation or support for further assistance.

References:

• Which version of Windows Server should I upgrade to?
• Upgrade on-premises infrastructure that supports Configuration Manager