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2021 was a breakout year for ransomware, costing hundreds of millions of dollars in losses—with the largest known paid ransom set at 40 million. Learning how to detect and deal with ransomware threats is and will continue to be a critical priority for cybersecurity researchers and analysts. In order to perform an in-depth analysis of ransomware behavior on a larger scale, we analyzed multiple samples of infamous ransomware from recent years in a uniquely customized sandbox—including WastedLocker, REvil, Prometheus, Conti, and RansomEXXX. Our analysis proved successful in identifying key ransomware behavior characteristics across multiple metrics and led to the development of new and more effective methods of detection and mitigation.