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Over the last years, we faced an exponential growth of illegal online market services in the Dark Web, making it easier than ever before of acquiring illicit goods online via a simple service interaction. To study and understand this emerging illegal services economy, we developed a trend analysis and (dark-)web services monitoring tool: SENSEI, which stands for ‘Scraper for ENhanced analySis to Evaluate Illicit trends’. SENSEI extracts specific service transaction trends and analyses the human behaviours behind, to produce symmetric insights on specific service transaction habits from both customers and vendors on the Dark Web. Moreover, a trend analysis tool is provided to discover and typify relationships among different criminal activities and hence provide evidence and support investigation activities and Law Enforcement Agencies (LEAs) detecting criminal operations.