Digital Transformation (DT) holds strategic importance, with extensive research on its implications for Small and Medium-sized Enterprises (SMEs) gaining prominence. SMEs, constituting a dominant force in the European economy, present unique organizational challenges in the DT landscape. Specific elements like resource constraints, leadership centrality, and distinct organizational structures significantly influence the DT process. While DT induces transformative changes across various dimensions, the dynamic environment, coupled with resource scarcity, gives rise to organizational paradoxes in SMEs, a facet often overlooked in existing literature focused on large enterprises. Our research aims to address this gap, exploring the nuanced impact of SME-specific features on inherent paradoxes during DT. Rooted in two preliminary exploratory studies, our findings highlight the importance of analyzing paradoxes within SMEs, emphasizing their association with organizational peculiarities. Effectively managing these paradoxes is crucial for SMEs navigating the complexities of DT and ensuring enduring success.