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During the last decades, Dark Web content has risen in necessity in an increasingly connected world, where international anonymous networks provide access to data marketplaces and illicit multimedia material through the TOR or I2P networks. The motivation behind this paper is to gauge the current state and growth of the Dark Web in relation to the role it plays with special focus on Small and Medium-sized Enterprises (SMEs and MEs). More specifically, we devise Machine Learning and specialised Information Retrieval techniques to extract insights and investigate how the Dark Web enables cybercrime, maintains marketplaces with breached enterprise data collections and pawned email accounts. The research questions that we address concern: a) the role that the Dark Web plays for SMEs, MEs, and society in general; b) the criticality of cybercriminal activities and operations in the Dark Web exploiting threat …