Scholars have recognised digital agricultural technologies and financialization as important vectors of agri-food transformation, yet little research has examined how these trends mutually influence one another. In this paper, we present case studies of four firms that blend together digital agriculture, farmland investment, and finance capital in novel ways. Veripath is an established farmland investment company, with significant holdings in Western and Central Canada. It relies on digital technologies to remotely monitor the performance of its properties and the farming practices of its tenants. Farmers Edge is a digital agriculture platform and service provider founded in Canada in 2005, with operations spanning North America, Brazil, and Australia. The firm has received significant backing from finance capital and is partnering with U.S. farmland management services provider Farmers National Company to facilitate data flow among farmers, landowners, and investors. Finally, we present the cases of AcreTrader and FarmTogether, two recently launched farmland investment platforms promising to ‘democratise’ farmland investment by offering investors a seamless online experience for buying rural properties. We analyse how these firms represent an evolving nexus between finance capital and digital agriculture, with implications for agri-food restructuring.