You’ve seen this image a thousand times. Just your typical client walking into a gas station, stopping to think for half-a-second if they should download the app to order and pay online. The words, “pay here” (“compra aqui”) make it seem effortless. The happy model customer enjoying their donut looks innocuous. You might not recognize the subtle aggression beneath the surface. This advertisement, and the technologies and practices it encourages, symbolically and materially enact a mundane digital displacement of labor, tasks migrating from workers to clients, labor to capital. These mutations in labor are “retrogressive,” sliding from hi-to-low productivity as work is offloaded onto clients who must download the app, input their contact, link a payment, find their purchase, and receive a confirmation code just to pick up their donut! How are these technologies interpreted, negotiated, and implemented among workers, owners, and management in Small and Medium-Sized Enterprises in Chile? What are their expected returns and how are these returns distributed under increasingly unequal socioeconomic terms? These focal questions drive my research on digital technology adoption. The photo was taken while traveling to interview SME owners about their digital adoption technologies, strategies, and experiences.