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If both instances of the Windows desktop operating system on my PC are accessing Windows Server, do I need a device CAL for each instance of the operating system on my device?

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If both instances of the Windows desktop operating system on my PC are accessing Windows Server, do I need a device CAL for each instance of the operating system on my device?

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No. One device CAL is all that is needed for multiple operating system instances on a single physical machine. In the case of a User CAL each person accessing the server through any client device must have a CAL.

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