The main purpose of the paper is to analyse the procedures of urban brownfield solutions, with a focus on the environmental and cultural-historical aspects. The paper explores the dilemmas of brownfield regeneration and redevelopment. These processes are placed in the wider perspective of multi – transformation processes of post-communist cities. We compared two former industrial zones – Karolina and the Lower Area of Vítkovice in the city of Ostrava – where we illustrated the key factors influencing their transformation. These case studies point to a unique example of urban industrial brownfields concentrated within the area around the city centre, surrounded by residential zones. These brownfields also reveal the scope of the problem, as they are connected not only with the urban structure, but also with environmental, economic, social and cultural aspects. To research the issue in depth, we mostly used a qualitative approach to examine perceptions and to frame the brownfield issue. We partly applied frame analysis, a narrative approach and we also used research techniques such as document content analysis, and in-depth interviews with relevant stakeholders who are involved in the remediation of brownfields and their subsequent re-use (N₌15). We researched how stakeholders perceive and frame the problem and which solutions they prefer. Moreover, having made a comparison of the state of affairs between 2001 and 2012, we presented a deeper insight into the topic. We found quite a wide range of opinions toward the brownfields issue and its solutions. The main issues were related to people striving to find the identity of the city and the tension between the old and the new: looking for the direction of future development and the face of the city of Ostrava. We identified location, level of environmental degradation and social-economic conditions as the main factors that influence the brownfield issue.