Achieving national renewable energy targets presents multi-level governance challenges, such as uneven progress and discrepancies arising from varying subordinate specifications and incentives on wind energy development. Governments have commenced adopting ‘positive planning’ that aim to integrate energy targets with spatial and land use planning, yet detailed discussions regarding wind energy development remain scarce. This paper assesses three cases in Germany and Sweden within criteria-based explanatory case studies to provide planners and policy makers with knowledge on key factors, lessons learned, and challenges. Positive planning appears to center on a strong energy target focus, limited space, and a balanced approach, shaped by the socio-political context. While Germany more recently embraces positive planning, Sweden started ambitiously on a national level but encounters policy and planning challenges. Planning agencies play an important role in promoting wind energy targets at mid-scale levels; however, 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-off between species protection and renewable energy and offering municipal incentives. Nonetheless, satisfactory spatial trade-offs for long-term proof of concept remains a challenge.