Digital transformation has become an urgent necessity for enterprises in the Hashemite Kingdom of Jordan to keep pace with economic and competitive challenges, improve operational efficiency, and expand access to new markets. This study aims to highlight the readiness and importance of small and medium-sized enterprises (SMEs) transitioning toward a digital economy. To achieve the study’s objectives, a descriptive-analytical methodology was employed, focusing on examining and describing the achievements and challenges by analyzing the current digital landscape for those enterprises. Data was collected through a questionnaire, with 350 responses obtained out of 363 distributed electronically to a sample consisting of managers of SMEs, resulting in a response rate of 96%. The study found that SMEs in Jordan are active in digital transformation despite facing financial and technical challenges, the most prominent of which was the lack of allocated financial resources necessary to cover the costs of the transformation. Among the most notable achievements were increased sales and exports for enterprises pursuing digital transformation. The study recommended several key measures, most importantly intensifying governmental and private sector support for these enterprises to help them catch up with larger digital enterprises in the Kingdom, as well as enhancing their employees’ digital skills through workshops and training programs.