Problem Definition:


As of January 14, 2020, Microsoft will be officially ending all support for 2008R2 Windows servers. This doesn't mean that your server will suddenly stop working, but it does mean that you'll be at a drastically increased risk for malicious attacks. To counteract this, the best course of action is to upgrade your server to a more recent operating system. 


Resolution:


There are two routes as a solution to the incoming end of support: deploy an entirely new, more current system, or upgrade your current system from Windows Server 2008 R2 to Windows Server 2016, which is detailed below.


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 2008R2 Windows Server (Windows 7 Emulated) to Windows Server 2016 (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.


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


Expected time of completion: 4-6 hours


Log Into your vCloud Director Instance


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

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.


Create a snapshot of the server for rollback purposes


Ensure only the "Quiesce" box is checked.


Ensure the snapshot completed successfully


Insert media into the VM


Mount most recent Upgrade Prep. As of publication of this article, the most recent version is V372. Always use the most recent version.


Double-check that you're logged in to your virtual server as a Domain Administrator


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


Eject Upgrade Prep ISO


Insert CD/DVD from Catalog


Insert the Windows Server 2012 R2 iso


Login as a Domain Administrator


Run the 2012 R2 Server upgrade


Begin server software installation


Install security updates


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


NOTE: ALL CITRIX MACHINES WILL REQUIRE A GUI.


Note: If you get an error regarding, it is because you might have selected the wrong operating system to install. Simply click the prompt to move back to this screen, and select the correct operating system version.


You might see this prompt; if you do, disregard it. The operating system MUST be updated to ensure maximum security and performance. This step WILL take a while.

This step WILL take a while.


Once the software is finished installing, log in to the machine as a Domain Administrator


Eject Windows Server 2012 R2 iso


Note: If you'd like to stay on Windows Server 2012R2 (Windows 8.1 Emulated) click here to jump to the next relevant section. 


Insert CD/DVD from Catalog


Insert the Windows Server 2016 iso


Run the 2016 Server upgrade


Install security updates


Install the corresponding software to your Virtual Machine



NOTE: ALL CITRIX MACHINES WILL REQUIRE A GUI


Login to the VM as an Administrator


Eject the Windows Server 2016 iso


Insert CD/DVD from Catalog


Insert the most recent version of DesktopConfig. As of publication of this article, the most recent version is V401. Always use the most recent version.


Run DesktopConfig



Click OK at the Welcome Dialogue:


!IMPORTANT!: Desktop Config will have you restart multiple times. The prompt to resume DesktopConfig will not always appear on launch. 




>>>>>>>>>>BE SURE TO RUN DESKTOPCONFIG TO COMPLETION<<<<<<<<<<  


Select the Active Directory Security Group or Groups whom you wish to authorize to access this system.  If you are unsure, check the Remote Desktop Users Local Security Group on the system.  If you are using Citrix, leave the "Enable Citrix HDX Enhancment for RDS checked."  If you are not using Citrix in this environment, make sure this checkbox is cleared.


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:



If you see this Dialog Box, choose “Keep AppLocker’s existing configuration.”

If prompted with the following screen, make sure you Check the Box to “Upgrade the Citrix Virtual Desktop Agent.”  Leave the other options checked.


If Upgrading the Citrix Virtual Desktop Agent, the process may take up to 15 minutes and only a Blue PowerShell window will display.  Do not close this PowerShell window.  Please be patient.


When prompted, restart the system: This is the message you'll receive when DesktopConfig has run to completion. 


When you've finished with DesktopConfig, shut down Guest OS. 


Once the VM is powered off, navigate to Properties


Ensure the Operating System is correctly listed as the operating system you have installed.


Start the VM again


Ensure 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!


Congratulations, you're done!


Additional Information: 



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.