This article examines how and why landlords vary in their uses of eviction filings. Drawing on over four million property tax records, business filings, and court-ordered eviction documents over fifteen years in Boston, Massachusetts, I show that large landlords file evictions at two to three times the rates of small landlords, and this disparity is not driven by the characteristics of the tenants they rent to. Not only do large landlords file more often, but also over less money owed and more often as a rent collection strategy. Drawing on analyses of the interpersonal conflict during eviction and a range of landlord characteristics, I show that these divergent eviction practices derive from the disparate social and institutional contexts within which landlords make eviction decisions. For small landlords, organizational informality and personal relationships with tenants make eviction a morally fraught decision, while for large landlords, formal decision-making and arms-length relationships with tenants make eviction a routine business practice. By showing both how and why landlords use evictions differently, this article contributes to the sociological understanding of residential instability and of landlord behavior.