Achieving national targets on renewable energy poses several challenges, especially in multi-level governance environments. Incentives and specifications on wind energy development might cause uneven progress or even discrepancies. Therefore, governments have commenced adopting ‘positive planning’ to combine energy targets with spatial and land-use planning. Yet detailed discussions regarding wind energy development remain scarce. In this paper, I explore three explanatory case studies in Germany and Sweden, aiming to provide policymakers and planners with essential knowledge while presenting significant challenges and key lessons learned. Positive planning appears to center on a strong energy target focus, limited space, and a balanced approach, shaped by the sociopolitical context. While Germany has recently embraced positive planning, Sweden started ambitiously but is encountering planning and policy challenges. Planning agencies play a vital role in promoting wind energy targets at mid-scale levels, yet legally binding targets matter. Striking a balance between energy targets and addressing land-use concerns without disregarding them requires managing a delicate trade-off. Early communication and inter-agency collaboration, as seen in Sweden, might facilitate identifying compromises, navigating trade-offs between species protection and renewable energy and offering municipal incentives. Nonetheless, negotiating satisfactory spatial trade-offs for a long-term proof of concept remains a challenge.