Cities stand up as a major concern for environmental governance and democracy, and an ideal target for theoretical investigations and practical innovations alike. Our work is concerned with reconstructing the links between democracy and the environment, by targeting urban governance and tapping into the institutional practices of Urban Planning and Strategic Environmental Assessment (SEA). SEA is a major policy tool, and its interplay with planning unravels key issues in both urban governance and environmental democracy, including coping with fundamental risks, voicing non-human agents, managing commons, addressing environmental justice. The observations we present in this paper rest on two parallel approaches. First, we carried out a content review of 12 SEA reports concerning urban plans in Italy. Second, we were involved in two case studies concerning urban planning and SEA in the towns of Monopoli and Magenta. We point to some key reflections with the aim of opening up the discussion. Participation often languishes in institutional arenas, yet it thrives in other forms that affect decision-making. Negotiation around individual planning processes should be framed in the general governance arrangements that are constantly reshaped through interactions among fluid trans-organizational networks. Legally binding measures have an ambivalent relation with environmental governance strategies, and they are handled with difficulty by deliberative planning approaches. In mainstreaming new policy tools (such as SEA), procedural aspects are usually stressed, whereas a focus on process and desired outcomes could foster, respectively, capacity building and salience