PowerEdge: In-place Upgrade Guidelines for Windows Server 2022

Operating system server upgrade process

1. Locate the Windows Server Setup media of the image that you target to upgrade to and then run setup.exe. 
2. Select Yes to start the setup process. For Internet-connected devices, select the Download updates, drivers, and optional features [recommended) option, and then select Next.
3. Setup checks your device configuration, you must wait for it to finish, and then select Next.
4. Depending on the distribution channel that you received Windows Server media from (Retail, Volume License, OEM, ODM, so on) and the license for the server, you may be prompted to enter a licensing key to continue.
5. Select the Windows Server edition that you want to install and select Next.
6. Select Accept to accept the terms of your licensing agreement, based on your distribution channel (such as, Retail, Volume License, OEM, ODM, and so on).
7. Select Keep personal files and apps to choose to do an in-place upgrade and then select Next.

After Setup analyzes your device a prompt appears to proceed with the upgrade by selecting Install.

The in-place upgrade starts and presents the Upgrading Windows screen with its progress. After the upgrade finishes, the server restarts.

See Upgrade Windows Server 2016 to Windows Server 2019 for additional information.

Scope of testing

Though in-place upgrades of the Windows Server operating system are not supported by Dell Technologies, this document is designed to highlight a few important observations. This testing is basic testing of the operating system and a few hardware features on an operating system upgrade performed on standalone server configurations.

The following is the overall scope of the effort, but does not encompass or cover all the possible operating systems nor hardware features of the peripherals like storage devices, network cards, so on. The focus is on the standalone server configurations. 

The hardware configurations and the upgrade scenario tested are outlined below:
 

The various features and roles tested are listed below:

Upgrade procedure

Requirements - operating system DVD of Windows Server or signed ISO images downloaded using My Account or the Microsoft MSDN site. 

Also please check the prerequisites before performing the upgrade by following this Microsoft article:

Perform an In-Place Upgrade of Windows Server | Microsoft Learn

 
Key points about upgrades are provided below: 

1. Update the base operating system with the latest available patches before the upgrade to the target operating system. (updates available from Windows Update)
2. All the hardware peripherals such as storage controllers and network cards should be updated with the latest firmware and drivers before starting the upgrade. (Updates available from Dell Support )
3. The user should ensure that the running applications are supported on the targeted (upgraded/new) operating system version
4. Changing of the language is not permitted while performing the upgrade

Recommendations or best practices

1. Create a backup of the data before initiating the upgrade. 
2. If the Errorhandler.command must be used across the migration, it should be copied to %WINDIR%\Setup\Scripts. ErrorHandler Command is a custom script that runs automatically when Setup encounters a fatal error

Important points to check after the upgrade is complete.

1. Check any logged errors in the event viewer [Ex: Any service failed or suspended] and take the required remediation steps
2. Check for any yellow bangs or device failures using device manager

Observations

• Upgrade of the operating system deployed on ISCSI LUN did not complete. "The installation failed in the SAFE_OS phase with an error during Boot operation." The operating system is reverted back to the current version
• If the Out of Box (OOB) drivers of the current operating system are having versions less than the inbox driver of the target operating system, then during the upgrade the inbox driver replaces the OOB driver. Failures can be observed as the inbox driver might or might not support the same features being supported by the OOB driver
• BitLocker service is suspended during the upgrade process under some scenarios. If the service is in the suspended state post the upgrade, it must be manually restarted. In our testing, the service functions seamlessly once manually restarted. This observation is for upgrade from Windows Server 2019 to Windows Server 2022 and an upgrade from Windows Server 2016 to Windows Server 2022

Additional information regarding the procedure and compatibility matrix for SQL servers while performing operating system upgrade can be found below.

Using SQL Server in Windows 8 and later versions of the Windows operating system

Supported version & edition upgrades (SQL Server 2019)

Tips for troubleshooting

Follow the links below for a comprehensive documentation on how to resolve the commonly occurring errors during an upgrade. 

Log Files

Resolve Windows 10 upgrade errors: Technical information for IT Pros