The technology associated with the Internet is said to evolve at the speed of light. That is certainly true when it comes to understanding the strategies and tactics used to commit cybercrimes, whether those crimes target military, governmental or private-sector organizations, and whether the threat actors are governments, government sponsored hackers, criminal cyber-gangs or individuals. In this paper, we examine recent evolutions of cyberspace threats to move them from simple and direct to more layered complex and stealthy methodologies. For example, what appears to be a ransomware attack encrypting files with the hope of collecting a ransom payment for a decryption key may actually hide the actual theft of that data, representing an actual data compromise. Suggestions for maintaining and improving an organization’s readiness to deal with these hybrid threats are provided.