Upgrading to both Windows 10 1903 and 1909 with Configuration Manager

The time has come to do another creator update to the corporate systems. We skipped the 1903 upgrade because of the Windows 7 to Windows 10 deployment that completed just after the release of 1903. It was too soon to start another creator update project, so we waited until 1909. One of the new features we are wanting is the reserved space that was introduced in 1903. This reserves seven gigabytes of data for future updates and upgrades. The feature is set by default when an OS is installed during a build. It has to be turned on after the OS is deployed during an upgrade via a registry key. The problem is that once the key is set to one, the reserved space does not take effect until the next creator update. Another major issue I had was that the task sequence can only execute one OS upgrade at a time. This is because once the upgraded OS is installed, it will continue running the same task sequence during the upgrade process. The screenshot below shows where it executes the rest of the task sequence. There is no way to circumvent this process. If it continues with the following OS install, the task sequence errors out.

To get both OSs installed within the same task sequence, I set up the EndTS variable that stops the second install if the first one has executed. This means the same task sequence will need to be run twice to install both versions. The trick is to set the Rerun behavior to Rerun if succeeded on the previous attempt, as shown below. This allows for the task sequence to be executed a second time. It will skip over the first upgrade, 1903, and go right to 1909. If 1909 is already installed and the task sequence reruns, the top-level folder sequence will prevent it from executing any other tasks. The other trick to stop this from running again after both installs are complete is to have the collection filter out systems that have 1909 installed.

The first thing you want to do is to import the desired Windows 10 versions as an Operating System Upgrade in the configuration manager. Once the OS Upgrades are imported, one thing you might want to consider is copying the content to a distribution share so that you can access the package in remote offices in the event of an OS upgrade failure, as shown below. This will allow you to be able to manually execute the install on a failed machine remotely for further troubleshooting.

Next will be creating the task sequence. You will want to create a new task sequence to upgrade an operating system from an upgrade package.

Stepping through the process of creating this task sequence is self-explanatory. I am going to include screenshots of each screen.

Here is what the task sequence looks like after I got it set up and added all of the necessary features. Your task sequence will likely be somewhat different, as every company has a unique configuration.

This is the conditional WMI query I use for the top-level Upgrade folder. This is so if the latest OS version is already installed, then it will skip over all other task sequences.

The next thing I have it do is to set the task sequence variable EndTS to 0. This variable is used to skip over the second OS upgrade if the first one runs. It does this by including a task sequence under the first OS upgrade that sets the variable to one. When the second OS upgrade task sequence is executed, there is a rule to only run if the EndTS equals zero.

The PowerShell 7 upgrade is next and simply run the PowerShell 7 application installation.

Here are the specs for the Check Readiness for Upgrade:

One of the specifications we have is that laptops are left in the office and docked. The following PowerShell script does just that as a condition for continuing the task sequence:

I had a lot of problems getting the cleanmgr.exe to work and was never successful. I saw on several sites where others had the same issue. I ran across Fabian Castagna's PowerShell script that does much of the same as cleanmgr.exe does. I could never get it to delete the windows.old folder, but I have a solution further on in this blog.

For the first upgrade, Upgrade the Operating System to 1903, I used the WMI filter so that it will only install it if the OS is older than 1903.

The next step is installing the OS. This step readies the system for the actual upgrade that takes place in the proceeding reboot.

The reboot step will restart the system, at which point the actual upgrade will take place. The OS does not load in this step. I have a 60 second wait time along with a message in the event a user is on the system at 1:00 am when the task sequence starts.

The next sequence is to Enable Reserved Storage. This is where a registry key is set that enables this feature upon the next upgrade.

REG ADD HKLM\SOFTWARE\Microsoft\Windows\CurrentVersion\ReserveManager /v ShippedWithReserves /t REG_DWORD /d 1 /f

The next sequence reruns the disk cleanup script.

Next comes deleting the Windows.old directory. I worked on this for quite a while. It is not easy to do if you can't automate cleanmgr.exe. It ended up being a hit or miss thing. Sometime the script I had written would work, other times, it either was unsuccessful, or it crashed the OS when it deleted the files still being used as a service. What I came up with was to remove the entire folder at once within WinPE. The OS does not load, so no files are in use, thereby allowing for the complete deletion.

The first thing is to boot into WinPE.

The next step is to delete the folder using the following PowerShell code:

 $Drive = Get-PSDrive | Where-Object {($_.Provider -like 'Microsoft.PowerShell.Core\FileSystem*') -and ($_.Description -like 'Windows*')}  
 If (Test-Path ($Drive.Root + 'Windows.old')) {  
      $Argument = '/c RMDIR.exe' + [char]32 + '/S /Q' + [char]32 + $Drive.Root + 'Windows.old'  
      $ExitCode = (Start-Process -FilePath ($env:windir + '\system32\cmd.exe') -ArgumentList $Argument -PassThru -WindowStyle Minimized -Wait).ExitCode  
 }  

Next comes a reboot using the currently installed OS.

Now comes setting the EndTS variable to 1, so the following OS upgrade does not execute.

The next step is the 1909 upgrade. The only differences in this compared to the 1903 update are:

• The Task sequence variable will be a condition set for the top-level folder of this task sequence
• Enable Reserved Storage task sequence is not needed
• End Task Sequence is also not required. 

Here are the conditions to run this set of task sequences that are set on the Upgrade the Operating System to the 1909 folder. We don't want this to execute unless 1903 is installed, and we don't want it to run if the task sequence just installed 1903.