A method, system and a computer program product are provided for obscuring web searches by performing cognitive analysis on the one or more user search inquiries to identify a user search behavior profile and user characterization information for the first user and generating or retrieving one or more simulated user search behavior profiles for one or more simulated users, and then generating one or more obfuscating search inquiries consistent with the one or more simulated user search behavior profiles for issuance with the user search inquiries to impair the search engine from accurately determining the user characterization information for the first user.