Against the backdrop of the coordinated advancement of the Digital China and Healthy China initiatives, this study uses panel data from 30 provinces in China from 2014 to 2024 to construct a comprehensive evaluation index system for the digital economy and multi-level medical security. Employing the entropy method, the coupling coordination degree model, kernel density estimation, the obstacle degree model, and the optimal parameter geographic detector, the study systematically examines the spatiotemporal evolution, obstacle factors, and driving factors of the coupling coordination between the two systems. The results show that: (1) the development levels of both the digital economy and multi-level medical security continued to improve, and their coupling coordination degree generally shifted from disorder to coordination, showing a spatial pattern of “higher in the east than in the west, and higher in coastal areas than in inland areas”; (2) the main obstacles are concentrated in the level of digital industrial development, the basic tier of medical security, software business development, and the coverage of medical assistance; and (3) information development and residents’ consumption capacity are important driving factors, and the interactions among factors generally exhibit a dual-factor enhancement effect.