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Over the past 30 years, Lithuania has faced numerous crises and significant events that have influenced the development of its cities, most of which have experienced not only population shrinkage but also economic, social, and infrastructural decline. Since 2020, urban trajectories have unfolded in parallel with a period of polycrisis, characterized by the simultaneous presence of the COVID-19 pandemic, geopolitical instability, the war in Ukraine, shifting international migration regimes, and region-specific migration pressures. These overlapping conditions have coincided with notable changes in demographic and economic patterns, raising questions about how urban shrinkage and resilience are expressed under sustained uncertainty. This paper examines the demographic development of medium-sized, post-industrial Lithuanian cities during the polycrisis period, focusing on three regional centers – Šiauliai, Panevėžys, and Alytus. Situated between metropolitan cores and peripheral areas, the cities play a key role in polycentric urban system, yet remain particularly vulnerable to demographic decline and structural change. Rather than isolating individual crises, the analysis situates observed demographic trajectories within the broader polycrisis context, attending to the interplay between macro-level disruptions and locally specific conditions shaping urban development. The study draws on a geocoded dataset linking register-based and census data for the entire Lithuanian population from 1992 to 2023. The findings reveal uneven demographic development and indicate that some medium-sized cities may be entering phases of stabilization or reconfiguration following prolonged decline. By focusing on non-metropolitan, post-socialist cities, the paper contributes to broader debates on urban shrinkage, resilience, and regional development under sustained uncertainty. • Polycrisis conditions reshape demographic and urban development trajectories. • Crises act as turning points that can unlock new urban opportunities. • Medium-sized post-industrial cities evolve differently even under analogous conditions. • City trajectories diverge due to combined effects of macro- and micro-level factors.