This paper presents a case study of farmers’ recent transition from growing traditional crops to cultivating sugarcane under a contract farming arrangement in Magobbo, Zambia. Responding to the need for a greater understanding of how the expansion of large-scale commercial agriculture impacts women, this study examines women’s control over resources, employment and labour, and impacts on their livelihoods. The research revealed that existing gender inequalities were perpetuated within new forms of agricultural production, but that widows experienced unique benefits compared to married women through increased status and income. A brief exploration of the gains and risks of commercialization in Magobbo illustrates there are significant benefits derived from the switch to sugarcane production, but also threats to the sustainability of those gains. Overall, this paper contributes to understanding the complexities of agricultural commercialization through contract farming arrangements, and the resulting gender and livelihood implications.