The growing interest in rotational crossbreeding in Western countries is due to its potential to improve reproductive and health performances of cows. Although a large amount of research focuses on assessing crossbred cows’ performances, how to manage the transition from purebred to rotational crossbred herds is under-explored. Based on a retrospective analysis of French dairy herd case studies, we aimed to identify and characterise technical pathways to make such a transition. In 2018, we performed semi-directive interviews on 26 commercial dairy farms. Data were collected to describe changes in breeding, replacement and culling management practices from the first crossbred mating with purebred cows to the management of a mainly crossbred herd in 2018. Based on a multivariate analysis, we identified two main guidelines structuring technical pathways to move towards rotational crossbred herds: (i) the depth and scale of change (i.e. farm v. herd) associated with the introduction of rotational crossbreeding in the whole-farm dynamics and (ii) the changes in herd replacement and breeding practices to adapt to the evolution of herd demographics induced by the evolution of the dairy crossbred mating rate over time (high from the beginning v. distributed over time). Hierarchical clustering discriminated three groups of farmers differing in their technical pathway to move towards a rotational crossbred herd. In pathway 1, farmers customised one or several rotational crossbreeding schemes to support whole-farm transition towards an organic or grass-based system. Once the scheme stabilised, they quickly implemented it and had to readjust replacement and culling practices to regulate imbalance in herd demographics induced by the improvement in cow fertility. In pathway 2, farmers also customised one or several rotational crossbreeding schemes to support whole-farm redesign but they implemented it more gradually in the herd, which induced no major imbalance in herd demographics. In pathway 3, farmers predefined a relatively well-known rotational crossbreeding scheme to correct fertility issues of purebred cows without any changes at the farm level. They implemented it quickly from the beginning and had to adapt herd replacement and culling to regulate imbalance in herd demographics induced by the improvement in cow fertility. These first empirical evidences on how dairy farmers manage the transition from a purebred to rotational crossbred herd provide original scientific and operational contributions.