The present invention relates to an information security risk analysis automation system and a method of operation thereof. An embodiment of the present invention is a system for providing an information security authentication service, comprising: a management server for operating at least one of a website and a mobile app providing the information security authentication service; Including, the management server, the control to generate at least one question information to output through at least one of the website and the mobile app, and receives at least one answer information corresponding to the at least one question information And, based on the at least one answer information, a system for generating and outputting at least one of information on confidentiality, information on integrity, and information on availability is proposed.
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