India as a country is rapidly changing due to an influx of Information and Communication Technologies (ICTs). The impact of ICTs has been felt on far-flung areas ranging from agriculture to industry. In this chapter, we highlight possible ways in which ICTs can be included in the trucking sector from the bottom-up. In order to accomplish our goal, we present an ethnography with a sociotechnical dimension. Specifically, we recognize that large-scale social systemic challenges shape individual actions in the technological trucking sector. The ethnographic study comprised of semi-structured interviews with over 30 stakeholders, was conducted in the metropolitan port city of Mumbai, India. It was aimed at understanding the functioning of the sector, current practices, roles of stakeholders involved, and the challenges faced by them. The results are followed by a discussion that deals with the impact new information technology is having on the sector and identifies areas for future intervention.