Windows Server: Cannot Keep Files and Settings During In-Place Upgrade

Summary: An in-place upgrade of Windows Server does not allow files, settings, and apps to be kept. This option is disabled, and "Nothing" is the only available option. This occurs if evaluation media is used to perform the upgrade. ...

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Symptoms

When performing an in-place upgrade of the operating system (OS), the option to keep files, settings, and apps is not available:

Screenshot showing that "Nothing" is the only available option
Figure 1: "Nothing" is the only available option during the in-place upgrade.

There is no way to enable or select the other option.

Cause

This occurs if OS evaluation media is used to perform the in-place upgrade. Evaluation media is intended to be used for a clean installation of the OS rather than an in-place upgrade. Microsoft states this (somewhat obliquely) here:

https://learn.microsoft.com/en-us/windows-server/get-started/upgrade-conversion-optionsThis hyperlink is taking you to a website outside of Dell Technologies.

Resolution

To resolve this issue, perform the in-place upgrade using non-evaluation OS media. Both options should then be enabled.

Affected Products

Microsoft Windows Server 2016, Microsoft Windows Server 2019, Microsoft Windows Server 2022, Microsoft Windows Server 2025
Article Properties
Article Number: 000345922
Article Type: Solution
Last Modified: 16 Jul 2025
Version:  1
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