This chapter focuses on AI-based cognitive and perceptual enhancements. AI-based brain enhancements are already under development, and they may become commonplace over the next 30–50 years. We raise doubts concerning whether radical AI-based enhancements transhumanists advocate will accomplish the transhumanists goals of longevity, human flourishing, and intelligence enhancement. We urge that even if the technologies are medically safe and are not used as tools by surveillance capitalism or an authoritarian dictatorship, these enhancements may still fail to do their job for philosophical reasons. In what follows, we explore one such concern, a problem that involves the nature of the self. We illustrate that the so called transhumanist efforts to “merge oneself with AI” could lead to perverse realizations of AI technology, such as the demise of the person who sought enhancement. And, in a positive vein, we offer ways to avoid this, at least within the context of one theory of the nature of personhood.