Urban shrinkage is among of the most dangerous current risks for the preservation of liveability (e.g. residential function) in formerly prosperous historical residential and industrial districts. The planning for shrinkage emerged only in the 21st century in order to manage and prevent growing urban decay, depopulation and housing crisis through the application of smart structural adjustment policies and planning instruments for formerly heavily industrialised North American and Asian cities. Both shrinkage and liveability planning are still very “fuzzy” concepts and have been applied in ways that are not always consistent (e.g. for measuring decline, migration, demographics). However, remains the question of what (methods or approaches) would prevent (control) this well-known but evidently “wicked” and still less explored phenomenon of “loss of liveability” in a historical built environment. This paper aims to review the urban shrinkage and liveability problematic and prevention solutions (methods) based on studies of theory and practice of urban planning.