Landlord technology—or the systems used by landlords to control and regulate tenant lives, spaces, and data—frequently promises “frictionless” building management and residential experiences. Yet services such as “digital doormen” and virtual property management platforms often create more work for tenants, particularly regarding decreased accessibility for tenants of color whose faces are unrecognized by biased algorithms used to administer building access, and for renters who are unable to or who refuse to use new apps and web portals. There are also “digital butlers” that landlords deploy as a means of attracting and retaining wealthy residents, yet that end up creating increased and often gendered work for those laboring behind the curtains of automation. Even virtual property management tools rely upon outsourced labor and are rife with contradictions and hardships for renters and call center workers alike. With a proposition that new forms of material and affective labor are created by landlord technologies despite promises of frictionless living, this article focuses on the various struggles that workers and tenants face in using, maintaining, refusing, and, at times, organizing against property automation. Based upon collaborative research produced with Landlord Tech Watch, as well as ethnographic accounting of housing and labor struggles in New York City and Cluj, this article introduces friction as a critical analytic useful in assessing the uneven, gendered, and racialized labor formations that landlord technologies require and reproduce despite fictions of frictionless living.