“Proletarian” relations are generally understood in terms of capitalist dispossession. However, a deeper historical approach to class relations in Iceland reveals fundamental role of monopolization and labor insecurity across capitalist and precapitalist political economies. During the first settlement of Iceland in the late 9th century, land was freely available to colonists, but by the late 17th century, over 95% of all farming properties were owned by landlords. Landlords and tenants frequently negotiated new leases, effectively creating a dispossessed, insecure, and mobile class of tenant farmers. Using the millennium-long history and archaeology of farmsteads in Skagafjörður, Northern Iceland, we then outline 1) how it is that these “proletarian” relations came about in the first place, 2) how they were maintained and 3) finally how Iceland’s “transition to capitalism” in the late-19th and early-20th centuries was less the creation of a uniquely proletarian class but rather a migration of long-dispossessed labor under new capital regimes.