The concept of ecosystem services (ES) arises as a formal outcome of historical processes of understanding and interpreting settlements as complex ecological systems. Because of a straightforward, bottom-up demand for environment enhancement, this concept increasingly occurs in discourses, in narratives, in the demands of common people, triggering a new urban environmental awareness. This is now often arising spontaneously in the protocols of participatory plan processes, especially when planning for the future of complex environments such as city areas. The present study tries to elicit reflections around the significance of ES issues awareness in the case study of Bari (Italy), which is experiencing an inclusive and participatory process of construction of shared knowledge for the new master plan. Starting from an initial campaign of civic walks (CWs) along the urban neighborhoods and a subsequent semi-structured interview to the community, the paper carries out comparative analyses using problem-structuring methods (PMs), in order to evaluate and reflect on community behaviors and expectations about ES. Then the paper ends by emphasizing the role of structured knowledge-raising approaches, as critical activities to enhance ecosystem awareness in planning settlements as complex ecological systems.