It's no question that modern advances in AI and Deep Learning technologies have allowed organizations to greatly scale their defensive capabilities. Between detecting evolving threats, automating discovery, fighting dynamic attacks, and even freeing up time for IT professionals; AI-fueled automation has been a boon for system defenders. But before we get too comfortable, we need to remember that there is another side to this fight. In this talk, we'll take a look at how AI technologies are enhancing adversarial capabilities and how challenges in defensive machine learning are opening up new attack surfaces.