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In-Place Upgrade to Windows 10 1909 November 2019 Update (19H2) with MDT

2019-11-12: Microsoft have confirmed on Twitter that there will be no updated ADK for Windows 10 1909, so keep using ADK 1903 with the fix as noted below.

2019-10-24: At the time of writing there is no ADK for Windows 10 1909 November 2019 Update (19H2), so I’ve tested this walkthrough using the ADK for Windows 10 1903 with the hotfix for Windows System Image Manager. I’ll keep these pages up to date when Windows 10 1909 is officially released.

Current Known Issue: With the Windows 10 1903 ADK on 64-bit, the Windows System Image Manager (WSIM) will fail to generate a catalogue. Microsoft has issued a fix which you can download here. The fix contains two updated files, ImageCat.exe and ImgMgr.exe which need to be copied to the location the ADK is installed. By default the location is: C:\Program Files (x86)\Windows Kits\10\Assessment and Deployment Kit\Deployment Tools\WSIM.

After installation you will still not be able to access the WSIM through MDT, but launching WSIM manually and then opening the install.wim file for the Operation System you wish to change, and the XML answer file which will be located in \\server\share\Control\Task-Sequence-ID\Unattend.xml.

Lifecycle Support Notes from Microsoft: If you are using Enterprise or Education editions of Windows 10, from 1809 onwards the ‘09 versions of Windows 10 will get 30 months of support and the ‘03 versions will only get 18 months. So you may want to consider if you deploy the ‘03 versions at all and just stick to the ‘09 releases. Here’s the official information on the Windows lifecycle from Microsoft here.

Remember when in place upgrades of Windows were bad? Well, they’re much better now and it’s a good thing too because Windows as a Service (WaaS) depends on constant upgrades at least once every 30 months. This article will go through installing MDT, it’s dependencies and setting up a deployment share to upgrade existing Windows 10 devices to version 1909. In this article we’ll be focusing on the 64-bit Enterprise edition of Windows 10. This process will not work with custom images created using the traditional MDT build and capture process. So you cannot build a reference image like in my previous post and use the resulting image to upgrade a computer to the latest version of Windows. There are other utilities such as the excellent OSDBuilder by David Segura which you can use to build an image to use in an MDT (and SCCM) in-place upgrade Task Sequence.

Here are the links to the software we’ll be using:

Installing Microsoft Deployment Toolkit and Dependencies

  1. First we’ll install the Windows 10 1903 ADK. During setup additional files will need to be downloaded, so it may take some time depending on your internet connection.
  2. On the Select the features you want to install screen select:
    • Deployment Tools
    • Imaging And Configuration Designer (ICD)
    • Configuration Designer
    • User State Migration Tool (USMT)
  3. WinPE is now a separate install. Install the WinPE add-on by running the adkwinpesetup.exe, there is no specific configuration during the install wizard.
  4. Now install MDT by running the setup file downloaded earlier. There is no specific configuration during the install wizard.

Creating the Deployment Share

  1. Open the Deployment Workbench from the Start Menu.
  2. Right click on Deployment Shares.
  3. Select New Deployment Share.
  4. Enter the path for the Deployment Share: E:\Deploy.
  5. Enter the Share name: Deploy$.
  6. Give the share a description.
  7. On the Options screen, accept the defaults as you can change them later.
  8. Complete the wizard to create the share.
  9. By default, the share permissions are set the local administrators group. We’ll revisit this later.

Adding an Operating System

  1. Mount the Windows 10 1909 ISO in File Explorer.
  2. Go to Deployment Workbench > Operating Systems.
  3. Right click and select New Folder.
  4. Enter the name Windows 10 1909 x64 and click through the wizard to create the folder.
  5. Right click again and select Import Operating System.
  6. In the wizard, select Full set of source files and then enter the root of the mounted ISO as the Source directory.
  7. For the destination directory name enter Windows 10 1909 x64 and complete the wizard.
  8. Go to the Operating Systems/Windows 10 1909 x64 node and rename the new entries added to Windows 10 1909 Edition x64 for ease of use.

Creating a Task Sequence

  1. In Deployment Workbench, go to Task Sequences.
  2. Right click and select New Task Sequence.
  3. For the ID enter: IPU-W10-1909.
  4. Name it In-Place Upgrade Windows 10 1909.
  5. Select Standard Client Upgrade Task Sequence.
  6. Select the Operating System Windows 10 1909 x64.
  7. Select Do not specify a product key at this time.
  8. Enter an Organization name.
  9. Select Use the specified local Administrator password.
  10. Specify the password to use.
  11. Complete the wizard.

Now we’ll configure the Task Sequence.

Configuring the Task Sequence

  1. Right click on the Task Sequence just created and select Properties.
  2. Go to the Task Sequence tab on the Properties window of the Task Sequence.
  3. Expand the Preparation folder, and select the Gather local only item.
  4. Select the radio button Gather local data and process rules.
  5. Enter customsettings.ini in the Rules file: text field.
  6. Go to the Post-Processing folder and select Windows Update (Pre-Application Installation).
  7. On the right side of the Properties window, go to the Options tab.
  8. Uncheck the Disable this step tick box and do the same with Windows Update (Post-Application Installation).
  9. If you wish to run any custom scripts, putting them in between the Windows Update steps is a good place to put them.
  10. Click Apply and close the Task Sequence.

Next, we’ll create a domain user account for MDT for use as a service account.

Creating a service account for MDT in Active Directory

  1. Go to Active Directory Users and Computers.
  2. Create a user called mdt_admin and give it a complex password.
  3. Go to the Server or PC where the Deployment Share is hosted.
  4. Give the user mdt_admin Full Control share permissions and Full Control permissions to all the files and folders in the Deployment Share.

Next we need to configure the Bootstrap.ini and the CustomSettings.ini files to control certain aspects of the deployment environment.

Configuring CustomSettings.ini

On the Rules tab of the Deployment Share properties window, add the settings below. A lot of the settings are specific to my lab environment such as my location in the world. The [Virtual Machine] section near the top is one example of how to manage drivers and auto fill computer names.

Priority=Model, Default, SetOSD
[Virtual Machine]
DriverGroup001=Virtual Machine
TimeZoneName=GMT Standard Time

Running the In-Place Upgrade Task Sequence

I’ve tested my IPU Task Sequence on a VM running Windows 10 1803. My VM is joined to a domain, customised, had UWP apps removed and has Office 2016, Adobe Reader, Google Chrome and Adobe Flash installed.

  1. From within Windows 10 navigate to \\MDT-SERVER\Deploy$\Scripts and run the LiteTouch.vbs script.
  2. After a short delay you will be presented with the Windows Deployment Wizard and a list of the Task Sequences available.
  3. Select the Task Sequence we created earlier: In-Place Upgrade Windows 10 1909 and click Next.

The upgrade will take some time to run but once complete, it will be upgraded to version 1909. You may also want to add other applications to install as part of your upgrade Task Sequence.

I take great care to test my ideas and make sure my articles are accurate before posting, however mistakes do slip through sometimes. If you have any questions or comments please leave them below.

I hope this article is useful to you. Please consider supporting my work: PayPal.


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