Pope Francis imbued the ancient word parrhesia with new significance, framing “frank, bold, courageous speech” as a partner concept to his signature vision of a “listening church.” After tracing Michel Foucault’s genealogy of the term, I argue that Francis’s pneumatological turn is a creative ressourcement of parrhesia, one that would require major shifts for the present church to embrace. To illuminate the challenging intra-ecclesial dynamics of parrhesia, I analyze three case studies of figures from Vatican II whose frank, bold, courageous speech met institutional backlash. I conclude with implications for realizing a more parrhesiastic culture in a synodal church.