In 2021 we got windows 2019 servers from AWS, not the software requires windows server 2025. We are moving the Windows 2025 AWS model but need to retain files, apps and settings.

Hi Troy Soult,

How is your issue going? Has it been resolved yet? If it has, please consider accepting the answer as it helps others sharing the same problem benefit too. Thank you :)

VP

Hi Troy Soult,

The reason you cannot keep your files and settings during the in-place upgrade is that you are attempting to use the Windows Server 2025 Evaluation edition media against a production operating system. Microsoft's setup engine intentionally blocks data migration paths from a fully licensed volume or retail installation directly to an evaluation copy, grayout out the option to keep personal files and apps. To successfully perform this N-2 in-place upgrade from Windows Server 2019 Datacenter to 2025 Datacenter, you must obtain the official Volume Licensing or Retail ISO that matches your current licensing channel.

You can verify your current edition channel by checking the EditionID string value located in the HKEY_LOCAL_MACHINE\Software\Microsoft\Windows NT\CurrentVersion registry key. Once you mount the correct non-evaluation media and execute the setup.exe file, the installer will recognize the matching licensing channels and permit you to retain your applications and settings. Performing this manual in-place upgrade is a perfectly valid workaround, especially since the AWS Systems Manager automation frequently stalls when dealing with newer OS architectures that it does not yet fully support in its runbooks.

After your manual upgrade completes, the server should automatically authenticate against the internal AWS Key Management Service. You can ensure this succeeds by verifying your security groups allow outbound traffic on TCP port 1688. If the instance fails to activate automatically, you can manually point the software licensing manager to the AWS KMS server by opening an elevated command prompt and executing slmgr.vbs /skms 169.254.169.250 followed by slmgr.vbs /ato to force the activation request.

Hope this answer brought you some useful information. If it did, please hit "accept answer". Should you have any questions, feel free to leave a comment.

VP

Windows Server 2019 Datacenter can be upgraded in-place to Windows Server 2025 Datacenter on nonclustered systems, but several conditions must be met and some roles/features may block the “keep files, apps, and settings” option.

Key points from supported paths and methods:

1. Supported upgrade path

• Windows Server 2019 → Windows Server 2025 is a supported in-place upgrade path for nonclustered systems.
• For nonclustered systems, Windows Server 2025 supports upgrading up to four versions at a time, and the table explicitly allows upgrading from Windows Server 2019 to Windows Server 2025.

2. Edition and media requirements

• In-place upgrade requires compatible edition and licensing type. For example, Datacenter → Datacenter is supported, but evaluation → retail/volume and some other combinations have specific rules.
• The Windows Server 2025 evaluation media can be used for in-place upgrade only if the current installation and the media support that scenario. If setup only offers a clean install (no option to keep files/apps/settings), it typically indicates one of the following:
  • The edition or licensing type does not match a supported upgrade path for that media.
  • The installation type (for example, Server Core vs Desktop Experience) does not match.
  • One or more installed roles/features do not support in-place upgrade.

3. Role/feature limitations

• Some roles and features do not support in-place upgrades and will cause setup to disable the “keep files and apps” option.
• For workloads such as IIS and file services, Microsoft recommends using migration instead of in-place upgrade when in-place is blocked or unreliable. Roles and features can be migrated to a new Windows Server 2025 instance using:
  • Windows Server Migration Tools for many roles and features.
  • Storage Migration Service for file servers and storage workloads.

4. Alternative: migration instead of in-place upgrade If setup continues to block the in-place upgrade option, the supported alternative is:

• Deploy new Windows Server 2025 Datacenter instances (for example, using the AWS 2025 images).
• Migrate roles and features from the 2019 servers to the 2025 servers:
  • Use Windows Server Migration Tools for supported roles.
  • Use Storage Migration Service for file servers and storage (source can be Windows Server 2019; destination can be Windows Server 2025).
• This approach preserves data and configuration while moving to the new OS version and hardware/VM image, and is the recommended path when in-place upgrade is not available.

5. General guidance

• Always take full backups (system and data) before attempting in-place upgrades or migrations.
• Verify that both source (2019) and destination (2025) servers are fully updated before migrating roles and features.
• Review the support lifecycle for Windows Server 2025 (support ends October 2034) when planning long-term.

Given that the Windows Server 2025 evaluation media currently only offers a clean install in this environment, the supported and reliable way to retain files, users, and settings is to treat this as a migration scenario: stand up Windows Server 2025 Datacenter instances and migrate roles, features, and data using Windows Server Migration Tools and Storage Migration Service, rather than forcing an in-place upgrade that setup is blocking.

References:

• Overview of Windows Server upgrades
• Feature update, clean install, or migrate to Windows Server
• Upgrade and conversion options for Windows Server
• Upgrade and migrate roles and features in Windows Server
• Storage Migration Service overview
• Windows Server containers for April 2025 (Out-of-band)