The senior generation’s unwillingness to relinquish managerial duties and retire is a globally recognized characteristic of intergenerational family farm transfer. This is despite the array of financial incentives put in place to stimulate and entice the process. Applying Rowles’ concept of ‘insideness’ as a theoretical framework, this paper brings into focus the suitability and appropriateness of previous and existing farm transfer policy strategies, by presenting an insightful, nuanced analysis of the deeply embedded attachment older farmers have with their farms, and how such a bond can stifle the necessary hand over of the farm business to the next generation. This research employs a multi-method triangulation design, consisting of a self-administered questionnaire and an Irish adaptation of the International FARMTRANSFERS Survey in conjunction with complimentary Problem-Centred Interviews, to generate a comprehensive insight into the intricate, multi-level farmer-farm relationship in later life. The overriding themes to emerge from the content analysis of the empirical research are farmer’s inherit desire to stay rooted in place in old age and also to maintain legitimate connectedness within the farming community by remaining active and productive on the farm. Additionally, there is a strong sense of nostalgia attributed to the farm, as it is found to represent a mosaic of the farmer’s achievements as well as being a landscape of memories. The paper concludes by suggesting that a greater focus on the farmer-farm relationship has the potential to finally unite farm transfer policy efforts with the mind-set of its targeted audience, after decades of disconnect.