This paper delves into the experiences of new-entrant women farmers in creating leadership roles in community-supported agriculture (CSA) and how these experiences relate to the transformative potential of this agri-food model. It contributes to the literature on gender relations in CSA and agri-food transformation more broadly by offering new insights into disidentification from the traditional “woman farmer” identity prescribed by capitalist agri-food systems. We present case studies of three women farmers in two different CSA initiatives in Portugal, using data from semi-structured interviews and participant observation, and analysing them through open coding. Our study demonstrates that a focus on disidentification strategies shifts attention to the analysis of dissent from the status quo, revealing the tensions and ambivalent effects that ensue. Disidentification and leadership roles were influenced by these women farmers’ family constellations, sexuality and agricultural backgrounds. Although CSA initiatives are conducive to women farmers’ emancipation, the absence of collective efforts to address unequal gender relations hinders their transformative potential. CSA initiatives tend to overlook power imbalances emerging from their internal micro-politics and neglect the ambivalent effects shaping their transformative efforts. These findings offer new insights into agri-food transformation from a gender perspective and emphasise the non-linear nature of transformation as women farmers continually disidentify from the traditional “woman farmer” identity, even as they create alternative power positions in CSA that align more with their aspirations and abilities.