Among many possible interventions in public transport finance and policy designed to enhance the attractiveness of riding public transport, one of the most extreme, which is seldom implemented, is the elimination of passenger fares, effectively making public transport “free” for riders (with operating costs paid from other funding sources). This article describes a fare-free public transport program in Tallinn, Estonia, launched in 2013, which has exhibited lower-than-expected increases in ridership. Evaluations of Tallinn’s fare-free public transport program are presented and synthesized, with a focus on program goals and how goals are met through program performance. Findings suggest certain flaws limit the program’s potential success since the program design is misaligned with its primary stated goals, and several program goals relating to external effects of fare reform cannot be evaluated. Although it would be valuable for transport managers in other cities to learn about this experience, the Tallinn fare-free public transport program provides scant transferable evidence about how such a program can operate outside of a politicized context, which was crucial to its implementation in Estonia.