In computer virology, advanced encryption algorithms, on the bright side, can be utilized to effectively protect valuable information assets of enterprises. Yet, on the dark side, they can also be of use for malicious attackers to conduct pernicious activities. This article attempts to discover the surreptitious features of ransomware and to address it in information systems security research. It intends to elicit attention from enterprises with regard to ransomware—a newly emerged cyber hackjacing threat using such encryption technology as RSA—and to help both academic researchers and IT practitioners understand the technological characteristics of ransomware, along with its severity analysis. As ransomware infections continue to rise, and attacks employing refined algorithm become increasingly sophisticated, data protection faces serious challenges. This chapter draws a ransomware extortion scheme, compares ransomware with other malware, and discusses future trends and research directions in an effort to cater to both practitioners and researchers.