Guidance for in-place upgrade of Windows Server 2012, Windows Server 2012 R2 to Windows Server 2016

Products

• VMware vSphere ESXi

Issue/Introduction

In-place upgrade of the guest operating system (between major OS release versions, such as Windows Server 2012 or Windows Server 2012 R2 to Windows Server 2016) is not recommended. The best practice is to install a new major OS releases in a new VM.

Support considerations:

Read OS vendor's documentation to ensure the specific upgrade scenario is supported, e.g., Overview of Windows Server upgrades , Perform an in-place upgrade of Windows Server

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If the OS vendor does not support a particular upgrade scenario, then VMware will not be able to provide support for such scenarios due to lack of ability to collaborate with the OS vendor.
In-place upgrade is a feature of the operating system, if problems are encountered, it is best to first contact the OS vendor for assistance. If the OS vendor has narrowed down problem to be specific to VMware software, then VMware can provide assistance.

Some VMware products do not support in-place upgrade of the guest operating system in a VM. For more details, see VMware support for guest operating system upgrade (2018695) .
Check VMware Compatibility Guide to ensure new operating system version is supported as guest on the VMware product.

Check the configuration of VM to ensure that it meets requirements to run new OS release. New major OS releases sometime increase the minimum require amount of memory, video ram, disk space, etc. In addition, performing OS upgrade consumes disk space, so ensure VM has adequate storage to complete the upgrade. It may be necessary to power off the VM to make some of these adjustments before starting the upgrade.
For all applications running in the OS, contact the application vendor to determine their support policies and guidance for conducting operating system upgrades.

Resolution

Before guest OS upgrade, upgrading VMware tools to the latest version available for current Windows release, test installation on a cloned VM firstly, taking snapshot of the VM or saving backup of the VM are recommended.

If you have a Windows Server 2016 ISO image used for Windows Server 2016 installation, you can follow below procedure:

1. Mount this ISO file to the VM, select “Virtual Machine -> Edit Settings -> CD/DVD drive -> Datastore ISO file”, click “Browse” to select the Windows Server 2016 ISO file from datastore as CD/DVD media.
2. Logon to the guest OS and double-click CD-ROM from the File Explorer.
3. Follow the installation prompts to complete the OS upgrade.
4. Upgrade or reinstall VMware tools after OS upgrade is done.
5. Shutdown VM, select “Virtual Machine -> Edit Settings -> VM Options -> General Options”, change “Guest OS Version” to “Microsoft Windows Server 2016 (64-bit)” or “Microsoft Windows Server 2016 or later (64-bit)”.

Additional Information

Known issues:

The vsock library DLLs for the vsock protocol are registered during vsock install by VMware Tools installer, this vsock protocol registration gets broken and lost over the OS upgrade, causing the socket creation requests fail.

Workaround:

Uninstall and reinstall VMware tools after OS upgrade.

Resolution:

This issue is resolved in VMware tools 11.3.0. For more information, see VMware Tools 11.3.0 Release Notes .