This article examines the activism of three women of different generations—Emilia Rodríguez Sotero, Baldramina Sotero Cervoni, and Isabel Rosado Morales—in the movement for Puerto Rico's independence in the twentieth century to demonstrate the sheer breadth of some of the strategies undergirding that struggle. It uses oral history to reveal the otherwise unseen interactions and emotional support that extended across political generations of women in Puerto Rico. The article argues that women independence activists followed a dialogic practice that contributed to the movement's endurance. They spoke across political generations and looked to the biographies of women they knew well to style their own activism and navigate profound institutional and cultural barriers against independence organizing. Such intergenerational exchange defies an easy inheritance model and instead presents a genealogy of women's activism that was dialectical in bridging each generation's experiences at the intersection of political work and private life.