Green (and blue) spaces receive attention as important components of cities that can help to mitigate the effects of climate change, support biodiversity and improve public health. Green space planning aims to transform cities towards urban sustainability and resilience. In a longitudinal study, representatives from eleven European municipalities that had previously been interviewed in 2014 were re-interviewed in 2020–2021 on changes in urban greening and related practices. The interviewees reported mainly advancements in dealing with ecological issues, such as new plans, strategies, regulations or funding programmes for climate adaptation or biodiversity support, as well as some progress in co-governance with non-governmental stakeholders. Promising developments include breaking professional silos by creating new units that can better deal with complex urban issues. In a few cases, high-level local politicians induced profound changes. These changes stimulated the development of new planning and governance cultures, resulting in more co-creation of urban green spaces. However, from a transformation studies perspective, incremental strategies dominate, and even when municipal representatives are aware that substantive changes are needed, they often lack the means to act. For more radical system change, significant extra efforts are needed.