Retail is undergoing profound change, driven by digitalization, shifting consumer behavior, and recurring crises. Small and medium-sized retailers face the challenge of using limited resources to leverage digital technologies, strengthen resilience, and remain customer-focused. This work examines how digital transformation reshapes the retail value chain, the opportunities and risks that arise, and the capabilities required to stay competitive. The work also explores consumer behavior, both in times of crisis and among vulnerable groups such as children. It analyzes how external shocks like inflation or pandemics influence purchasing decisions, what factors shape children?s consumer competence, and how the presence of small and large retailers differs on digital platforms. With an interdisciplinary approach, the work integrates concepts such as resilience, dynamic capabilities, and technology acceptance. It provides practical insights for designing future-proof retail models while raising awareness of the broader societal implications of digitalization in retail.