While Visegrad Countries (V4) countries are often grouped together, their small and medium enterprises (SMEs) show different trajectories in digital transformation, particularly in the integration of technologies that drive operational efficiency. This study explores the difference by assessing V4 SMEs’ mainly post-pandemic digital maturity. Research identifies four unique country profiles using data from the Digital Economy and Society Index (DESI) that are connected to national issues and policy initiatives. Key findings indicate that Poland has a great cloud adoption rate but lags in process integration and AI, Czechia's e-commerce leadership is plateauing, and Hungary's focused support initiatives are correlated with an increase in data analytics. Despite these distinct advantages, the V4 region is falling short of the EU average in core process automation and is not keeping up with the EU in AI. Key challenges include financial constraints, lack of digital skills, and limited strategic drive for transformation. Each country has implemented national digitalization strategies and support programs, often aligned with EU initiatives, to address SME-specific needs. The findings of this study indicate that general, one-size-fits-all policies are not acceptable. It presents the main idea that the degree to which SME digitalization assistance is tailored to a country's unique, empirically-identified obstacles—like skills gaps, strategic vision, or process redesign costs—determines how effective it will be.