Agroecological and technological innovations are two important approaches in the transition towards agricultural sustainability. We lack knowledge about how current agricultural contexts may influence future development pathways and the relative importance of the two approaches. This study explores the alignment between past uptake of agroecological and technological practices and future visions of agricultural development in seven European arable farming systems. By combining landscape mapping with farmer interviews, we first assessed the past adoption of agroecological and technological practices in each region. Then, we compared our findings with expert surveys about the future directions of agricultural development that can address local arable farming challenges. We found that in regions with intensive arable farming, agroecological approaches lagged behind the uptake of technological measures, both in the past and in future prospects. In low-intensity regions, we found large gaps between past uptake and future prospects of agroecological and technological practice adoption. These gaps need to be overcome in the context of future challenges of climate change adaptation and of environmental obligations. Our results indicate the need to take differentiated measures depending on farm management intensity and landscape conditions to enhance the future uptake of agroecological and technological solutions that can address the local challenges.