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We are automatically installing virtual machines using WDS and after installation manually installing updates until atleast KB2919355 which we need.

What would be the best way to make sure this update would automatically be added to all new installations?

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"The best" is subjective, but the easiest way would probably be to slipstream the updates into your image.

To paraphrase from the link:

  1. Use DISM to mount the WIM (dism /mount-wim /wimfile:”D:\DeploymentShare\Operating System\YourOS\Sources\install.wim” /mountdir:C:\Mount /index:1 or whatever).
  2. Add the packages (dism /image:C:\Mount /add-package /packagepath:PATH-TO-UPDATE).

Or, conversely,

  1. set up a fresh machine, have it fully update, and then run Start /w for /R \\UPDATEDMACHINE\C$\Windows\SoftwareDistribution\Download\ %f in (*.cab) do DISM /image:C:\Mount /add-package /packagepath:”%U”
  2. Unmount the WIM with Dism /unmount-wim /mountdir:C:\Mount /commit

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