Deploy Windows 10 Winclone image with JAMF Pro / Casper

This article covers the process of creating a macOS installer package of a Winclone image and deploying the package with the JAMF Pro. 

Using Winclone 6's package feature, it is easy to deploy Windows to a large number of Macs using JAMF Pro.  The basic steps covered are:

1. Install Windows 10 on the Boot Camp partition and prepare using Windows tools
2. Using Winclone 6 or later to clone the Boot Camp partition to a Winclone image
3. Deploy using JAMF Pro

Install Windows 10 and Prepare Windows

Following the instructions to prepare Windows for deployment:

https://support.twocanoes.com/hc/en-us/articles/115003143163

Boot back into macOS, not Windows.  If you boot into Windows, the setup process will start and you'll need to re-create the boot camp partition.  Once in macOS, you'll use Winclone Pro to capture the image and create a package.

Create Winclone Image of Boot Camp partition

1. Install Winclone Pro in macOS if it has not been installed already.  
2. It is recommend that you use block-based imaging when deploying to large number of Macs since it is a faster. You select block-based image creation in the preference prior to creating the image.
3. Next, create a Winclone image of the Boot Camp partition using the steps in this support article:

https://support.twocanoes.com/hc/en-us/articles/115001236586-Save-Boot-Camp-to-a-Winclone-Image

Create Package

1. Launch Casper Admin and add the package to the distribution point by dragging the package to Casper Admin.  
2. Once the package has successfully copied to the distribution point, drag the package to the configuration you use to deploy the Mac image:
   
   
3. Double click on the package in your configuration and select the "Install on boot drive after imaging" option:
   
   The "Install on boot drive after imaging" option will copy the entire Winclone package to the Mac partition after imaging the Mac side, but will make the restoring much faster. Make sure that you have allocated enough space on the Mac partition for the Winclone package as well as enough space for new Boot Camp partition.  If space is a concern, do not select this option, but restoring may be much slower.

Deploying

You can now deploy this configuration as you would any other Casper configuration.  For example, if you are restoring via Target Disk mode in Casper Imaging, it would look this this:

Note that order of operations for the workflow:

1. Drive is erased (Mac)
2. macOS is restored
3. On first boot of the Mac, the Winclone package will be installed.  This will create the Boot Camp partition (if that option was selected) and Windows will be restored.
4. On first boot of Windows, Windows will be configured via the Answer file and the first run script you installed in Windows.

Troubleshooting

If there are any errors, this article covers troubleshooting package based installs:

https://support.twocanoes.com/hc/en-us/articles/115003010123-Troubleshooting-a-Winclone-Package-Install

Timing:

To get an idea of timing, I deployed a basic macOS dmg created with AutoDMG and a 8 GB Windows 10 image using target disk mode:

• Block Based image restore of macOS: 29 seconds
• Copy Winclone image to restore Mac partition: 18 seconds
  (reboot into imaged Mac partition)
• Create Boot Camp partition and restore 8GB Windows 10 image: 3 mins, 1 sec.