In the period between the 1760s and the 1850s boatmen were the most important transport workers in early colonial eastern India, at least numerically. Unfortunately, they have received little scholarly attention so far. By looking at the regime of work, which surprisingly had strong bases in the notion of contract from as early as the 1770s, this article explores the nature of work, work organization, and resistance by boatmen. It argues that although work was structured according to the wage or hire-based (thika) contract regime, the social, political, and ecological conditions in which contract operated were equally crucial. The centrality of contract was premised upon how effectively it was enforceable and, in fact, historically enforced. Boatmen being one of the most important “native” groups with which the British were left on their often long journeys, this article suggests that contract helps to understand the formal “structure of work”, and the minute details of the journey help to understand the “world of work”, of which clandestine trade, weather, wind, rain, torrents, tracking, mooring, internal squabbling, and, not least, preparing food were some of the main components.