Information Technology (IT) ‘outsourcing,’ of which medical transcription in India is a part, has received relatively little attention from geographers. Most often, it has been bracketed more broadly within IT and its role in transforming transnational space-time configurations has been analyzed. IT outsourcing, more specifically, medical transcription outsourcing, which is the focus of this article, is not only marked by tensions, hierarchies, and ambivalences, it also reflects an emergent ‘imaginative geography’ of neoliberal globalization. This imaginative geography, as we argue in this article, is deceptively ambiguous because of its ambivalent articulation. Medical transcription outsourcing, for example, seems to operate on two contradictory registers, particularly in the United States and some European nations from where outsourcing to countries such as India is taking place. There is an acknowledgement and even celebration of the ‘flattening’ and inter-connectedness of different parts of the world, even while there is widespread criticism and fear of these transnational activities, as well as that of the non-western people engaged in them. The criticism and fear are often articulated in relation to instances of data theft. Nevertheless, a closer look shows that there is something more going on. We argue that such discursive constructions exemplify an imaginative geography that is rooted in an ambivalent desire for a reformed and recognizable ‘other’ who could be ‘best global citizens.’ This ambivalence undergirds a forked biopolitical strategy, which seeks to make the neoliberal worker docile and yet continually marks him/her as dangerous. We call this biopolitical strategy colonial governmentality to signify its forked operation as an art of government that seeks to define agenda/non-agenda (and not population or people), but continually draws upon colonial distinctions and practices.