I am using Windows Server 2008 R2, VMM, and Hyper-V.
Is there any way to roll out an installation of an application and the same .properties file (for silent install) to all the VMs at once?
SCVMM is not meant to configure or maintaining machine images; that's what SCCM is for. SCVMM is for managing Hyper-V Hosts and the 'resources' they contain.
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