Tolls were not only fundamental to the operation of early modern English markets, but also had the capacity to generate tensions that belied their seemingly unremarkable role in contemporary economic affairs. Yet, tolls and toll disputes have received little attention in studies of market regulation and have also been neglected in studies of the politics of grain supply and marketing. This article revives tolls as an object of enquiry and suggests that they occupied an ambiguous position within early modern English economic culture. Tolls raised complex questions about how self-interest operated in a society that conceptualized bargaining primarily in communal terms and emphasized the social and moral obligations that should underpin it. While this was arguably true of tolls on all goods, it was especially true of tolls on grain – a commodity that occupied a singular place in contemporary socio-economic relations. By examining how competing parties in toll disputes articulated and sought to defend their interests, and how their respective tactics changed over time, this article sheds new light on the dynamics involved in England’s transition from one way of thinking about economic activity to another.