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This paper examines the evolution of cyberextortion, which is defined as real or threatening actions combining computer intrusion, theft, destruction and modification of data, social engineering, and fear for purposes of unlawful economic gain. By examining the multiple forms of cyberextortion, such as ransomware, denial-of-service attacks, holding sensitive data/cloud computing spaces hostage, this paper examines the progression of cyberextortion via case study analysis across gambling websites and dating websites to the more recent critical infrastructure realms, such as financial institutions and healthcare. This paper demonstrates that there are different levels of criminal organization, distinguished by their complexity of division of labor; coordination of roles; purposefulness of association between criminals; and ability to avoid, evade, or neutralize security systems and law enforcement.