This article provides an overview of an ongoing study that explores farm management practices by Australian women cotton growers using farm management software, most particularly agricultural decision support systems (DSS). The research methodology is interpretive with multiple case studies of women cotton growers and industry professionals. Participants were selected on the basis of indicating an awareness of environmentally responsible and high technology farming practices. Data collection was principally by semi-structured in-depth interviews. The study is informed through a theoretical framework of structuration theory as a metatheory for probing the recursiveness of farm management and technology usage, and diffusion of innovations theory as a lower-level theory for analysing the characteristics of the software. Evidence from the study suggests that farm women intentionally select specific software modules for implementation depending on the attributes of the software. Further, while computer-based farm management systems, including agricultural DSS, are recognised media for technology transfer of industry research to farms, the study found the cooperation of farming partners to be essential in influencing effective reconstruction of farm management practices and software usage. The study also explores gender homophily, in particular the relationship between husband and wife as partners in a cotton farm business. It is apparent that gender differences and inequalities are still prevalent and indicative of “gender heterophily.” Nevertheless, in the main, communication between parties is harmonious, empathetic, and by definition homophilous, thus ensuring effective information exchange. A notable benefit of using decision support software is an enhanced critical awareness of existing farm management practices. Further, the women are empowered by increasing confidence to contribute in enterprising ways to a greater range of farm management tasks and to more innovative applications of computer-based farm management tools.