The story of the intra-anarchist controversy between Emma Goldman and Federica Montseny is yet to be told. One of their disagreements was the ideological impossibility of political collaboration: Goldman judged Montseny for serving as Minister of Health in the Republican government, while Montseny judged Goldman for being too detached from the reality of the Spanish Civil War. Instead of only drawing on biographical parallels, this contribution also focuses on both writers’ publications dedicated to the Spanish Revolution, which have never been subject to a comparative reading. This parallel analysis promises new insights on Goldman’s and Montseny’s stances on more general anarchist arguments, such as their take on feminism or carceral abolitionism, and on specific questions of the Spanish Revolution, such as the militarization of the formerly pacifist anarchist movement during the Spanish Civil War. This contribution aims to retrace both Goldman’s and Montseny’s political thought, using sources such as Radio CNT-FAI as well as contemporary newspapers and findings from the Emma Goldman Collection at the Tamiment Library Archive.