Much has been made about the impact of new technologies on the organisation of work in the professions. However, the gendered effect of technological change has rarely been a focus of investigation, even though these transformations are occurring in a context of persistent and pervasive gendered inequality. This paper aims to address this gap, using the case of the legal profession to understand the gendered impact of technological change. Drawing on insights developed through interviews with 33 senior legal stakeholders, the paper finds that technological change plays out in contradictory ways, offering both promise and peril for gender equality within the legal profession. We identify four key concepts – bifurcation, democratisation, humanisation, and flexibilisation – to elucidate the intricate interplay between technology and gendered legal careers, acknowledging the dual potential that technology holds for advancement and adversity. We argue for proactive measures and strategies to be adopted by legal institutions, professional associations, and employers, to harness the benefits of new technologies while mitigating the very real risks such technologies pose to a more gender-equitable future of work.