In the dynamic and highly competitive environment of Digital Transformation, where new solutions and technologies continually evolve, the growing demand from customers drives companies to continuously update their business models in pursuit of innovation. A large number of companies are classified as small and medium-sized enterprises (SMEs), and it is precisely these companies that face major challenges during the journey of Digital Transformation, including significant resource constraints, knowledge limitation, and a shortage of qualified workforce. Despite the extensive literature on Digital Transformation in large corporations, the application of these approaches in SMEs is limited. This article aims to fill this gap by highlighting the characteristics and specific constraints faced by SMEs when undertaking Digital Transformation projects. The adopted methodology included a review of existing literature and direct interviews with managers of SMEs. The study emphasizes the aspects and barriers faced by SMEs, offering strategic guidance for managers. The results identify challenges and provide a deeper understanding of constraints related to resources, human capital, and specialized knowledge, offering practical guidance for the success of Digital Transformation in SMEs.