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My company uses Anyconnect VPN of Cisco, and any company PC device is required AD username/password to access the network. I'm thinking about the case when an employee copies the whole windows (copy the whole disk) and put on a non-company device. Is there a way to detect this case? If yes, how to configurate to fire an alarm or notification when a non-company device tried to access the network?

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One could in theory use a computer's TPM to store a asymmetric key/certificate and use certificate authentication for the VPN.

Assuming there is no vulnerability in the TPM which allows the export of private key material, copying the Windows to a device which has not had it's TPM set up by the organization should be useless.

Everything else is fake-able by a sufficiently advanced adversary.

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