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Short-term land rental agreements such as the traditional conacre system in Northern Ireland offer flexibility between the landowners and the farmers renting the land. However, the uncertainty of tenure linked to such short-term land rental systems does not allow for farmers renting the land to make longer-term investment planning and decisions, particularly around sustainable land management practices. Long-term tenancy agreements have been identified as a viable option to cope with short-term uncertainties and improve the environmental management of the land. In this study, we analysed the factors influencing farmers’ intention to adopt long-term land leasing with and without income tax incentives in Northern Ireland. To achieve our objective, we employed ordered logistic regression models complemented with qualitative analysis. The results of our analyses showed that varying factors including risk attitude, pro-environmental behaviour, profit consciousness, having a dairy enterprise, the area of farmland owned, the presence of a successor, and the age and education of the farmer influence farmers’ intention to adopt long-term land leasing. However, variability exists depending on the farmers’ rental status and availability of income tax incentives. It can be concluded from the study that policies aimed at encouraging long-term land leasing should take a holistic approach that incorporates environmental and socioeconomic factors.