This paper focuses on how technology services can help small and medium-sized enterprises (SMEs) overcome the digital transformation dilemma of “cannot transform (lack of know-how), dare not transform (fear of risk), and have no money to transform (lack of funds).” Using literature analysis and multiple case comparisons, the study summarizes five major categories of technology services: technical support, consulting and planning, training and empowerment, resource integration, and financing connectivity. It constructs a “service–capability–performance” catalytic framework. Tracking of 58 enterprises in the Yangtze River Delta reveals that resource integration contributes the most to digital maturity, with absorptive capacity playing a significant mediating role; the configuration of “high technology services + high absorptive capacity + high environmental dynamism” is a sufficient condition for high transformation performance. Based on these findings, countermeasures are proposed, including improving the technology service system, strengthening government-industry-academia collaboration, and optimizing funding and talent supply, providing replicable experience for SMEs, governments, and technology service institutions.