Starting from the definitions and principles of the Historic Urban Landscape Recommendation adopted by UNESCO in 2011, this chapter critically reflects on how different urban conservation approaches cope with change in three European World Heritage cities: Bordeaux (France), Florence (Italy), and Edinburgh (UK). By discussing the findings of a comparative analysis of existing urban conservation management policies, legislation, and tools, the chapter sheds light on good practices and critical aspects to support the improvement of urban conservation processes to better handle contemporary challenges in these case studies, but also in other historic urban landscapes in Europe and beyond.