Windows Server 2016 to Windows Server 2019 In-Place Upgrade (Step by Step)

This video show's how to do In-Place Upgrade (Step by Step) from Windows Server 2016 to Windows Server 2019. All require step mentioned along with supported versions.

[@user-ls9rs2vp4w]

how to fix ¨The Keep Personal Files And Apps Option Is Greyed Out¨ ?

[@antunezcarlos]

The ability to keep personal files and apps during an upgrade is dependent on the specific conditions and compatibility of your existing installation. If the option to "Keep Personal Files and Apps" is grayed out during the upgrade process from Windows Server 2016 to Windows Server 2019, it could be due to various factors, including:
1. Compatibility: Windows upgrades may require certain compatibility checks. If the existing installation has compatibility issues with the new version, the option to keep files and apps may be disabled.
2. Edition: Ensure that you are attempting to upgrade from Windows Server 2016 Standard to Windows Server 2019 Standard. Upgrading between different editions (e.g., Standard to Datacenter) may affect this option.
3. Licensing: Ensure that you have a valid license for Windows Server 2019 and that it matches the edition you are upgrading to.
4. Disk Space: Sufficient free disk space is required for the upgrade. Ensure that there is enough space on the system drive (usually C:) for the upgrade to proceed.
5. Administrative Privileges: Ensure that you are running the upgrade process with administrative privileges.
To resolve this issue and enable the "Keep Personal Files and Apps" option:
1. Verify Compatibility: Review any compatibility issues or error messages that may be displayed during the upgrade process. Resolve these issues if possible.
2. Ensure Licensing: Ensure that your Windows Server 2019 license is valid and matches the edition you are upgrading to.
3. Free Up Disk Space: Check the available disk space on your system drive and ensure it has enough free space for the upgrade.
4. Run as Administrator: Make sure you are running the upgrade process with administrative privileges. Right-click the setup file and select "Run as administrator."
5. Backup: Regardless of the option to keep files and apps, it's always a good practice to backup your important data and configurations before performing any major upgrade.
If the option is still grayed out after considering these factors, it might indicate a specific compatibility issue or limitation for your system. In such cases, you may need to perform a clean installation of Windows Server 2019 and then manually reinstall your applications and restore your data from backups.