Performing an in-place upgrade of Windows Server

If you have virtual machine (VM) instances running earlier versions of Windows Server, you can upgrade them to later versions of Windows Server:

Upgrade from Upgrade to
Windows Server 2008 R2 (Desktop Experience) Windows Server 2012 R2 (Desktop Experience)
Windows Server 2012 R2 (Core) Windows Server 2016 (Core)
Windows Server 2012 R2 (Desktop Experience) Windows Server 2016 (Desktop Experience)

If you plan to upgrade Windows Server 2008 R2 to a version later than Windows Server 2012 R2, you must:

  1. Perform an initial upgrade to Windows Server 2012 R2.
  2. Perform a second upgrade to Windows Server 2016 or Windows Server 2019.

This guide describes how to perform a manualm in-place upgrade of Windows Server. For upgrades from Windows Server 2008 R2 to Windows Server 2012 R2, you can also perform automated in-place upgrades by using the gcloud command-line tool.

Objectives

This guide describes how to perform an in-place upgrade of Windows Server by:

  1. Planning the in-place upgrade
  2. Performing the in-place upgrade
  3. Troubleshooting the in-place upgrade
  4. Cleaning up after the in-place upgrade

Costs

There is no charge for performing an in-place upgrade of Windows Server. You are only charged for the resources consumed during the upgrade, including:

Use the pricing calculator to generate a cost estimate based on your projected usage.

Before you begin

The guide assumes that you have basic knowledge of:

Planning the in-place upgrade

Performing an in-place upgrade of a virtual machine (VM) instance that is running an earlier version of Windows Server can be a pragmatic way to modernize your infrastructure and to mitigate the risks of approaching the end of the support lifecycle of Windows Server versions.

Alternatives to consider

Before you decide to use an in-place upgrade to migrate to a newer version of Windows Server, be aware of the following limitations:

  • Downtime: Depending on the configuration and software installed, the upgrade might take an hour or longer. During the upgrade, access to the VM instance is limited because:

    • Workloads running on the VM instance are unavailable to users
    • Remote Desktop Protocol (RDP) is not available
    • There are limited ways to check the upgrade progress and the time remaining in the upgrade
  • Risk: Depending on the configurations of your existing instances and the installed software:

    • The upgrade can fail
    • Some configuration options can be overridden
    • Incompatibilities can cause your workload to malfunction on the upgraded instance

Depending on the workload running on your Windows Server instance, you can reduce downtime and risk by pursuing different approaches.

Workload Approach
Your VM instance is running a workload that supports replication, such as:
  • Active Directory Domain Services
  • DNS
  • SQL Server
Consider setting up a new VM instance that is running a more recent version of Windows Server, and then use replication to shift the workload from your existing VM instance to the new VM instance.
You have a VM instance that is running a multitude of workloads Consider migrating these workloads to separate VM instances so that each VM instance runs only a single workload. Even if you can't migrate all workloads, reducing the number of workloads running on a single VM instance can help reduce risks during an in-place upgrade.

Product keys

A Windows Server product key is valid for only a specific version; when you perform an upgrade to a later version of Windows Server, you must supply a new product key. There are two primary scenarios:

  • You are upgrading a VM instance that is based on a public operating system image provided by Google: In this scenario, you must use the predefined KMS client setup keys for the version of Windows Server that you are upgrading to. The upgrade does not incur additional charges.

  • You are upgrading a VM instance for which you brought an existing license: In BYOL, you need to acquire a product key from your license vendor to perform the upgrade. Check the Microsoft documentation to determine which edition you can upgrade to and whether you are eligible for license conversion.

Installation media

To perform the upgrade, you need an installation media. There are two primary scenarios:

  • You are upgrading a VM instance that is based on a public operating system image provided by Google: In this scenario, you can use the volume license installation media provided by Google. The steps to access this installation media are provided below.

  • You are upgrading a VM instance that is based on an imported disk or image: In this scenario, you cannot use the installation media provided by Google. Instead, you have to use an installation media that matches the type of media that you used to install Windows Server on the imported disk or image.

Other prerequisites

Before you begin your upgrade, review the Microsoft documentation about prerequisites and potential limitations for the version of Windows Server you are planning to upgrade to:

2012 R2

2016

Performing the in-place upgrade

The following sections guide you through the process of upgrading your VM instance.

Creating a snapshot

Before you start the upgrade, we recommend that you create a snapshot of your VM instance, so that you can revert to a safe state in case anything goes wrong:

Preparing your Windows Server configuration

Verify the configuration of your Windows Server VM instance:

  1. Connect to your VM instance with an RDP client.

  2. Verify that Windows Server is up to date by using Windows Update.

  3. Disable or uninstall antivirus, antispyware, and other agents that can interfere with the upgrade or are incompatible with the Windows Server version that you're upgrading to.

Attaching the install media

Before you can perform the upgrade, attach the necessary installation media to the VM instance. The right media to use depends on your scenario:

  • You are upgrading a VM instance that is based on a public operating system image provided by Google: In this scenario, you only need to attach the volume license installation media provided by Google. This media contains both the necessary scripts to run the upgrade and the files for the new version of Windows Server.
  • You are upgrading a VM instance that is based on an imported disk or image: In this scenario, you also need to attach the volume license installation media provided by Google so that you can access the necessary scripts.

    Additionally, you have to attach a custom installation media that matches the type of media that you used to install Windows Server on the imported disk or image.

To attach the volume license installation media provided by Google, follow these steps:

  1. In the Google Cloud Console, open Cloud Shell by clicking the Activate Cloud Shell Activate Cloud Shell. button.

    Go to the Google Cloud Console

  2. Set the default project ID. Replace PROJECT_ID with the name of your Compute Engine project:

    gcloud config set project PROJECT_ID
    
  3. Create a disk based on the installation media. Replace ZONE with the name of the zone where the VM instance is located:

    gcloud compute disks create win-installers --image-family=windows-install-media --image-project=compute-image-tools --zone=ZONE
    

    This command adds a disk named win-installers to your project. This disk is not attached to any VM instance.

  4. Attach the disk to your VM instance by using read-only (ro) mode, so that you can attach the disk to multiple VM instances if necessary:

    gcloud compute instances attach-disk VM_NAME --disk=win-installers --mode=ro --zone=ZONE
    

    Replace the following:

    • VM_NAME: the name of the VM instance to upgrade
    • ZONE: the name of the zone where the VM instance is located

If you are upgrading a VM instance that is based on an imported disk or image, attach the custom installation media as an additional disk:

  1. Follow the steps in Creating an image from an ISO file to create a disk from the ISO image that you want to use as custom installation media.

  2. Attach the disk to your VM instance, by using read-only (ro) mode so that you can attach the disk to multiple VM instances if necessary:

    gcloud compute instances attach-disk VM_NAME --disk=CUSTOM_MEDIA_DISK --mode=ro --zone=ZONE
    

    Replace the following:

    • VM_NAME: the name of the VM instance to upgrade
    • CUSTOM_MEDIA_DISK: the name of the disk containing your custom installation media
    • ZONE: the name of the zone where the VM instance is located

Starting the upgrade

By default, Windows Setup prompts you for input at various points during an upgrade. Because you can't connect to the VM instance by using RDP during the upgrade and therefore can't provide any input, run the upgrade in unattended mode.

  1. Connect to your VM instance with an RDP client. For more information, see Connecting to instances.

  2. Open an elevated command prompt:

    • If you use Server Core, an elevated command prompt should open automatically after login.
    • If you use Windows Server with full Desktop Experience, right-click the Start button and select Command Prompt (Admin).
  3. Change the working directory to the installation media. The correct working directory depends on the Windows Server version that you are upgrading to:

    2012 R2

    cd /d d:\*2012*
    

    2016

    cd /d d:\*2016*
    
  4. Start the Windows upgrade. The required steps to start the upgrade depend on the Windows Server version that you are upgrading to and whether your VM instance is based on a public operating system image or on an imported disk or image:

    2012 R2

    Run upgrade.ps1 to start the Windows upgrade. The script completes the following steps:

    • Install the latest Google driver packages, which are critical for the Windows Server upgrade to succeed.
    • Apply Windows settings that are required for Compute Engine.
    • Enable access to the Emergency Management Services (EMS) console during the upgrade.
    • Launch Windows Setup (setup.exe) from the install media to perform an upgrade in unattended mode.
    • Select the correct edition of Windows Server 2012 R2 to install.
    • Provide a product key for the new version of Windows Server.
    powershell -ExecutionPolicy Bypass -File upgrade.ps1
    

    2012 R2 (imported)

    Run upgrade.ps1 to start the Windows upgrade. The script completes the following steps:

    • Install the latest Google driver packages, which are critical for the Windows Server upgrade to succeed.
    • Apply Windows settings that are required for Compute Engine.
    • Enable access to the Emergency Management Services (EMS) console during the upgrade.
    • Launch Windows Setup (setup.exe) from the install media to perform an upgrade in unattended mode.
    • Select the correct edition of Windows Server 2012 R2 to install.
    powershell -ExecutionPolicy Bypass -File upgrade.ps1 -SetupExePath SETUP_PATH -Unattend UNATTEND_PATH
    

    Replace the following:

    • SETUP_PATH: the path to setup.exe on your custom installation media
    • UNATTEND_PATH: the path to a custom unattend.xml file that contains a valid product key

    The -Unattend parameter is only required if you are upgrading a VM instance for which you brought an existing license (BYOL)

    2016

    Run upgrade.ps1 to start the Windows upgrade. The script completes the following steps:

    • Install the latest Google driver packages, which are critical for the Windows Server upgrade to succeed.
    • Apply Windows settings that are required for Compute Engine.
    • Enable access to the Emergency Management Services (EMS) console during the upgrade.
    • Launch Windows Setup (setup.exe) from the install media to perform an upgrade in silent mode.
    • Provide a product key for the new version of Windows Server.
    powershell -ExecutionPolicy Bypass -File upgrade.ps1
    

    On the Select Image screen, select the configuration that matches your current configuration:

    • If you currently use Server Core, select Windows Server 2016 Datacenter.
    • If you currently use Windows Server with full desktop experience, select Windows Server 2016 Datacenter (Desktop Experience).

    • Click Next to begin the upgrade.

    It might take several minutes for the setup to initialize.

    2016 (imported)

    Run upgrade.ps1 to start the Windows upgrade. The script completes the following steps:

    powershell -ExecutionPolicy Bypass -File upgrade.ps1 -SetupExePath SETUP-PATH -ProductKey PRODUCT-KEY
    

    Replace the following:

    • SETUP_PATH: the path to setup.exe on your custom installation media
    • PRODUCT_KEY: a valid product key for Windows Server 2016

    The -ProductKey parameter is only required if you are upgrading a VM instance for which you brought an existing license (BYOL).

    On the Select Image screen, select the configuration that matches your current configuration:

    • If you currently use Server Core, select Windows Server 2016 Datacenter.
    • If you currently use Windows Server with full desktop experience, select Windows Server 2016 Datacenter (Desktop Experience).

    • Click Next to begin the upgrade.

    It might take several minutes for the setup to initialize.

    The upgrade process might issue the following warning. If so, you can ignore it:

    [package name] or a newer version is already installed on the system
    

    After about 5 minutes, the machine reboots, and RDP disconnects.

Observing the upgrade process

Depending on the machine type of your VM instance and your Windows Server configuration, the upgrade might take between 10 and 60 minutes to complete. During that time, you can observe the status through the serial port output:

  1. In Cloud Shell, observe the boot process by running the following command:

    gcloud compute instances tail-serial-port-output VM_NAME --zone=ZONE
    

    Replace the following:

    • VM_NAME: name of your VM instance
    • ZONE: name of the zone where the VM instance is located
  2. Wait until the machine has rebooted four times. Depending on the configuration of your VM instance, it might take 30 minutes or more for these reboots to occur. You can recognize a reboot by output that looks similar to this:

    SeaBIOS (version 1.8.2-20190620_103534-google)
    Total RAM Size = 0x00000001e0000000 = 7680 MiB
    CPUs found: 2     Max CPUs supported: 2
    
  3. After the fourth reboot, wait until the output GCEMetadataScripts: Finished running startup scripts or No startup scripts to run appears.

Performing post-upgrade steps

You can now connect to the VM instance to verify that the upgrade has been successfully completed.

  1. Connect to the VM instance by using an RDP client. For more information, see Connecting to instances.

  2. Log in using a user account with local administrator privileges.

  3. Open an elevated command prompt:

    • If you use Server Core, an elevated command prompt should open automatically after login.
    • If you use Windows Server with full desktop experience, right-click the Start button and select Command Prompt (Admin).
  4. Run the following command to query the version of Windows Server:

    ver
    

    Verify that the version matches the expected version of Windows Server.

  5. Change the working directory to the installation media. The correct working directory depends on the Windows Server version that you are upgrading to:

    2012 R2

    cd /d d:\*2012*
    

    2016

    cd /d d:\*2016*
    
  6. Run upgrade.ps1 again to re-apply specific Compute Engine settings that might have been lost during the upgrade:

    powershell -ExecutionPolicy Bypass -File upgrade.ps1
    
  7. Restart the VM instance to ensure all changes take effect. It might take 1 to 2 minutes for the reboot to complete before you can connect to the VM instance again.

Detaching the installation disk

You can now detach the installation disk from the VM instance:

  • In Cloud Shell, detach the installation disk from your VM instance, replacing VM_NAME with the name of your VM instance:

    gcloud compute instances detach-disk VM_NAME --disk=win-installers
    

Installing updates and restoring access

After the upgrade is complete, run Windows Update to download and install any security updates. To install these updates:

  1. Connect to the machine by using an RDP client. For more information, see Connecting to instances.

  2. Use Windows Update to install the latest Windows updates. You might have to restart the VM instance multiple times during this process.

  3. Re-enable any agents, antivirus, or antimalware software that you disabled before the upgrade.

Troubleshooting the in-place upgrade

While running Windows Setup, you can't connect to the VM instance with RDP. If you suspect that the upgrade failed or is not progressing, use the following approaches, in order, to diagnose the situation:

Check the serial port output

To check the progress of the upgrade process, view the serial port output of the VM instance:

  • Serial port 1 captures the boot status
  • Serial port 3 captures the log output of Windows Setup

During the upgrade, you should observe four reboots. If you don't observe any progress for more than 30 minutes after the first reboot, it is likely that the upgrade failed.

Check CPU and I/O metrics

Running a Windows Server upgrade is a CPU and disk I/O intensive operation. By checking the CPU and I/O metrics, you can get an indication for whether the setup is progressing.

View the CPU and I/O metrics in the Google Cloud Console:

  1. In the Cloud Console, click the instance that you're upgrading.

    Go to the Cloud Console

  2. Click the Monitoring tab.

Connect to the Emergency Management Services console

Both during and after running Windows Setup, you can connect to the Emergency Management Services (EMS) console. Using the EMS console, check the Windows Setup log files and the event log for indications that the upgrade is still progressing or for information about any errors that might have occurred.

Connect remotely by using WinRM

If connecting by using RDP or EMS fails, you can try using WinRM to establish a remote PowerShell session:

  1. Connect to a different Windows Server instance in the same VPC.

  2. Open PowerShell.

  3. Establish a remote PowerShell session, replacing VM_NAME with the name of the instance to upgrade:

    Enter-PSSession -ComputerName VM_NAME -UseSSL -SessionOption (New-PsSessionOption -SkipCACheck) -Credential (Get-Credential)
    
  4. When prompted for credentials, enter the username and password of an administrative user account.

  5. Use the remote PowerShell session to check the Windows Setup log files and the event log.

Analyze log files offline

If you can't connect to the instance by using Windows Remote Management (WinRM), you can cancel the upgrade and analyze the log files from a different VM instance. To do this:

  1. Stop the VM instance.

    This can take several minutes if Windows Server is unresponsive.

  2. Detach the boot disk from the instance.

  3. Create a new, temporary Windows Server instance, and attach the boot disk of the original instance as an additional disk.

  4. Use the temporary Windows Server instance to analyze the setup log and event log files of the instance that you were trying to upgrade.

  5. After you have completed the analysis, detach the disk from the temporary instance and reattach it as a boot disk to the original VM instance.

Troubleshoot RDP

For information about troubleshooting RDP, see Troubleshooting RDP.

Troubleshoot your Windows Server instances

For information about troubleshooting your Windows Server instances, see Tips and troubleshooting for Windows instances.

Cleaning up

To avoid incurring further costs after you have completed this process, delete the installation disk.

Deleting the installation disk

You can create an installation disk based on the Google-provided image at any time. If you don't plan to upgrade more VM instances in the same zone, delete the installation disk:

  • In Cloud Shell, delete the win-installers disk that you created earlier:

    gcloud compute disks delete win-installers
    

What's next