This chapter focuses on the technological gaze, as that which determines the looking relations that human subjects hold with technology, using capitalist machines. These objects, things, or devices shape how human subjects engage with reality, since they play instrumental roles in the extent to which what human subjects see become relegated to technologically mediated looking relations with reality. In utilizing bell hooks’s conceptualization of the oppositional gaze, this chapter outlines how the technological gaze becomes oppositional, by transforming human subjects (or users) into technologized subjects that are, in effect, subordinates in relations of technological power, through technological affirmation. In turn, through Karl Marx’s understanding of machinery and technology, the technological gaze sets the conditions for the technologically mediated looking relations that technologized subject have, so that their looking relations are relegated by the institutionalization of technologization. Given the institutionalizing effects of technologically mediated looking relations, technologized subjects are placed in subordinating positions of proletarianization, through technologized exploitation.