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Upgrade a Citrix Server Operating System

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Note: This article is for a virtual server that WAS deployed with Citrix or RDS capabilities. If your server was NOT deployed with Citrix or RDS capabilities, click here to be brought to the correct article. If you're not sure how your server was deployed, click here to determine which process you should follow.

CloudConnect has a catalog of all the software that you'll need to install, including images for each server iteration as well as proprietary software that will simplify and streamline the upgrading process. Usually, you would have to manually strip the virtual machine of it's Citrix or RDS settings in order to successfully upgrade operating systems. CloudConnect's "UpgradePrep" utility eliminates this. For the best security and longevity, this article will explain how to upgrade your 2012R2 Windows Server (Windows 8.1 Emulated) to Windows Server 2019 (Windows 10 Emulated).

Note: Please ensure that your virtual server has at least 20 GB of free storage space before you begin the upgrade process. You cannot increase the space of the virtual drive while a snapshot is active.

Process: Prior to beginning this procedure, make sure all Citrix or RDS Desktop Users are logged out of their Cloud desktops.

Expected time of completion: 2-4 hours

Log into your vCloud Director instance

Log in as a domain administrator to the server that you want to upgrade.

Note: Please ensure that your virtual server has at least 20GB of free storage space before you begin the upgrade process.  You cannot increase the space of the virtual drive while a snapshot is active.

Create a snapshot of the server for rollback purposes

Ensure only the "Quiesce guest file system" box is checked.  Press OK to create the snapshot.

Ensure the snapshot completed successfully

Insert media into the VM

Click the Filter icon and search for "Upgrade Prep".  Mount the most recent version of UpgradePrep.  As of publication of this article, the most recent version is V410.  Always use the most recent version.

Run Upgrade Prep

Create a unique local admin password.  This will be used to log in to the virtual machine if it gets disconnected from the Domain.

Go through the prompts, and restart the VM once Upgrade Prep has completed successfully

Eject the UpgradePrep ISO by selecting "Eject Media"

Next mount the Windows Server 2019 ISO to the virtual machine

Run the 2019 Server upgrade

Begin the installation and select "Not right now" for updates, drivers, and optional features

Install the corresponding software to your Virtual Machine.  Note: All Citrix Machines will require a GUI (Desktop Experience).

Be sure to select "Keep personal files and apps" and continue

You might see this prompt; if you do, confirm it.  The display driver will automatically be reinstalled through DesktopConfig

Press "Install" and let Windows upgrade the Operating System

Once the Operating System upgrade has completed:  Eject the Server 2019 ISO, and mount the most recent version of DesktopConfig

Run DesktopConfig

DesktopConfig will recognize that this is a post Operating System Upgrade configuration.  And apply the necessary configuration:

Press OK to reboot:

Run the DesktopConfig Utility again after reboot and press OK at the Welcome Dialogue:

Ensure you pick the proper Desktop Access group for this virtual machine and continue:

Generally you will not change any of the Desktop Options as selected.  If you are using Citrix, leave "Use an Existing Remote Desktop Deployment" unchecked:

Choose "Keep AppLocker's existing configuration".

Leave the default settings and press "Continue"

Once DesktopConfig has finished you will see this prompt.  Press OK for the final reboot!

Once you've finished with DesktopConfig, shut down Guest OS.  Once the VM is powered off edit the properties of the Operating System to match the newly installed Operating System.  Note: If Windows Server 2019 is not an available option, selecting Windows Server 2016 is OK as they use the same kernel.

Power on the VM again:

Ensure that you can log in as a regular Citrix user:

Select the desktop you've upgraded

Ensure everything is working properly.  If you're experiencing a performance issue, it might be because DesktopConfig didn't run to completion.

Finally, remove the snapshot.  After this, you're finished!

Please remember to remove the DesktopConfig media from the Virtual Machine once you are finished

Applies to: Windows Server 2012R2, Windows Server 2016

Additional Notes: 

If the Upgrade fails, take the following action:

1) Collect Logfiles located at C:\CloudConnect\DesktopConfig\

2) Open a Low Priority Support Ticket case with CloudConnect Technical Support, and attach your log files.

3) Rollback the upgrade by choosing "Revert To Snapshot" from the Virtual Machine's context menu.

4) Power On the Virtual Machine.

5) If users still cannot logon within 15 minutes of Powering On the Virtual machine after Reverting the Snapshot, escalate your Technical Support Request's Severity to Service Outage.

The CloudConnect Desktop Configuration Utility upgrades Remote Desktop Services and Citrix software components to the latest Cloudconnect-supported Configuration.  Desktop Configuration Utility does not upgrade the Windows Operating System.  For guidance on upgrading the Microsoft Windows Operating System in place, see CloudConnect Upgrade Preparation Utility.

Learn More: 

To learn more about how CloudConnect streamlines the process of upgrading Citrix or Remote Desktop Server operating systems, you can click here to download our latest Citrix whitepaper.