Through the lens of her jail journal and published works such as Tragedies of Kerry (1924) and The Irish Republic (1937), this article examines the manner in which Dorothy Macardle encoded her attitude to the Treaty split and civil war in constructions of masculinities. Male behaviour towards women was a signifier of the integrity or otherwise of political stance on the issue of the 1921 Treaty. Soldiers and officials of the Irish Free State were guilty of moral failure in their willingness to sanction violence against republican women in the civil war sites of incarceration and by acting in a similarly repressive manner as the British had previously acted against the Irish. In her writing, Macardle constructed a chronicle of the female prison experience during the civil war that marked the Free State official and solider as "other" in his boorishness to the courtly, dignified republican male.