Cyberattacks are the “new normal” in the hyper-connected and all-digitized modern world, as breaches, denial-of-service, ransomware, and a myriad of other attacks occur every single day. As the attacks and breaches increase in complexity, diversity, and frequency, cybersecurity actors (both ethical and cybercrime) turn to automating these attacks in various ways and for a variety of reasons, including the development of effective and superior cybersecurity defenses. In this chapter, we address innovations in machine learning, deep learning, and artificial intelligence within the offensive cybersecurity fields. We structure this chapter inline with the Lockheed Martin’s Cyber Kill Chain taxonomy in order to cover adequate grounds on this broad topic, and occasionally refer to the more granular MITRE ATT&CK taxonomy whenever relevant.