The City of Tallinn, capital of Estonia, with a population of 420,000, recently became the world’s largest municipality offering free public transportation. Tourists still have to pay to ride the city’s bus, trolley, and tram network, but registered residents—including a large population of Russian-speaking non-citizens—only have to tap their municipal transit cards once onboard. This article presents a qualitative account of the world’s largest free public transporta- tion experiment to date. The results challenge and inform the conventional measures and objectives of transportation experts. The analysis is meant to complement the existing literature surveying free public transportation experiments and evaluating transportation pricing schemes.