Free public transportation is often praised for assisting low-income groups that are more dependent on transit services and encouraging transit mode shifts. This article is a deep dive into Tallinn, the capital of Estonia, where fare-free transit has been implemented for a decade. Strangely enough, it finds the number of commuters has decreased ever since. Residents now own more automobiles and are more likely to drive. Transit commutes have fallen from over 40% in 2013, and commuters who drive increased from 40% to approximately 50%. Local leaders identified several reasons for this underwhelming response. Firstly, the country’s growing wealth prompted an increase in car purchases. Some economists consider public transit an inferior mode with less appeal. Thus, wealthier residents are less interested in taking transit. Other explanations include a shifting residential pattern (suburbanization) and limited transit access to suburban jobs. To effectively encourage a mode shift, researchers suggest the city to charge drivers for the societal costs of their vehicles. As cities become more affluent, more investments are needed to improve the quality and reliability of transit services when transit price becomes less of a barrier.