This paper explores the ambiguous impact of new information and communications technologies on the cultivation of moral skills in human beings. Just as twentieth century advances in machine automation resulted in the economic devaluation of practical knowledge and skillsets historically cultivated by machinists, artisans, and other highly trained workers , while also driving the cultivation of new skills in a variety of engineering and white collar occupations, ICTs are also recognized as potential causes of a complex pattern of economic deskilling, reskilling, and upskilling. In this paper, I adapt the conceptual apparatus of sociological debates over economic deskilling to illuminate a different potential for technological deskilling/upskilling, namely the ability of ICTs to contribute to the moral deskilling of human users, a potential that exists alongside rich but currently underrealized possibilities for moral reskilling and/or upskilling. I flesh out this general hypothesis by means of examples involving automated weapons technology, new media practices, and social robotics. I conclude that since moral skills are essential prerequisites for the effective development of practical wisdom and virtuous character, and since market and cultural forces are not presently aligned to bring about the more salutary of the ambiguous potentials presented here, the future shape of these developments warrants our close attention—and perhaps active intervention.