While crop diversification has many benefits and is a stated government objective across the Eastern Gangetic Plains (EGP) of South Asia, the complexity of assessment has led to a rather limited understanding on the progress towards, and status of, smallholder crop diversification. Most studies focus on specific commodities or report as part of a singular index, use outdated secondary data, or implement highly localized studies, leading to broad generalisations and a lack of regional comparison. We collected representative primary data with more than 5000 households in 55 communities in Eastern Nepal, West Bengal (India) and Northwest Bangladesh to explore seasonally based diversification experiences and applied novel metrics to understand the nuanced status of farm diversification. While 66 crops were commercially grown across the region, only five crops and three crop families were widely grown (Poaceae, Malvaceae, and Brassicaceae). Non-cereal diversification across the region was limited (1.5 crops per household), though regional differentiation were evident particularly relating to livestock and off-farm activities, highlighting the importance of cross border studies. In terms of farmer's largest commercial plots, 20% of systems contained only rice, and 57% contained only rice/wheat/maize, with substantial regional diversity present. This raises concerns regarding the extent of commercially oriented high value and non-cereal diversification, alongside opportunities for diversification in the under-diversified pre-monsoon and monsoon seasons. Future promotional efforts may need to focus particularly on legumes to ensure the future sustainability and viability of farming systems.