Countries promoting renewable energies encounter a variety of phenomena that can challenge the implementation of further onshore wind energy development. Those challenges can be observed in many multi-level governance systems, as exhibited in the U.S., Germany, and Mexico, where various regulatory and institutional levels must agree on goals and responsibilities. This is a challenge, as both forms of governance (top-down and bottom-up dominated) are present in wind energy planning and policy. (1) Political and market phenomena, (2) siting issues, (3) the green vs. green dilemma, and (4) social acceptance are selected challenges within the different levels of decision-making processes in wind energy implementation. (1) Political and financial factors can influence the development by implementing incentive- and market-based policies, command-and-control policies, and feed-in tariffs. However, success of these policy designs for renewable energies is based on different political environments, and their electricity markets nationally, regionally, or statewide. (2) Spatial limitations in planning are created based on limited land availability due to conflicts with other land uses such as aviation, nature reserves, residential areas, their respective buffers. (3) The “green vs. green” dilemma involves the incoherent relationship between policies promoting renewable energies with policies protection species and their environments, becoming a major point of concern during siting and operations of wind energy. (4) Lastly, while there is a general overall support for wind energy, social acceptance on a local level is influenced by institutional settings i.e. information availability, as well as public and stakeholder concerns. Involvement in decision-making as well as financial participation (e.g. community-ownership) affects public participation and acceptance. This paper goes into detail on these phenomena and discusses case studies in Europe and North America. Often, these challenges can enhance outlooks in policy and planning, posing solutions to wind energy challenges even in sensitive environments and triggering innovations such as adaptive management.