SSL connections will fail to an IIS server that has been sysprep'd. Windows sysprep will change the SIDs on all the existing accounts. This will effectively remove access to the private key for the IIS account i.e. Network Service. In order to restore it, you'll need to remove the certificate from IIS, delete the certificate from the certificate store, and import the certificate again.
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Music expresses that which cannot be said and on which it is impossible to be silent. See the link below for more info.
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