The use of artificial intelligence (AI) in cybersecurity, while often overhyped, is not a new concept. Hackers have included countermeasures in malware since its inception to detect runtime environments or sense detection attempts. Early actions were primitive compared to what we know today, but they laid the groundwork for more critical thought about adaptive and evasive technologies and sophisticated situational awareness. This lethal combination of research and deep targeting is likely the future of malware as adversaries attempt to outsmart the companies and researchers trying to thwart them.