This chapter identifies three challenges to human wisdom posed by ongoing advances in robotics, machine learning, and computer automation. Building upon an account of wisdom as moral or intellectual expertise enriched by the habit of responsible self-regulation in the light of holistic value judgments, I note that in many future labor contexts, machine expertise, or the semblance of it, will appear to be an increasingly expedient and attractive substitute for human expertise and wisdom. Moreover, existing technical, political, and economic conditions may well disrupt the historical pattern in which automation eventually creates new and enriched domains for the cultivation of human expertise and wisdom. I conclude that unless we challenge these conditions and assume responsibility for their effects, we risk wasting the vast positive potential of artificial intelligence and automation, which lies in their only acceptable use: namely, enlisting their power in the full support of our own moral and intellectual perfectibility, in the service of the growth of human wisdom for the benefit of ourselves and those who share our world.