SMEs play an important role in all developed and developing countries contributing highly to employment, new business ideas, and the economy. However, owing to various challenges related to the modern digital environment and various limitations in terms of financial and technical capacities as well as digital literacy, there are numerous challenges that SMEs experience in improving their businesses’ performances through effective use of digital technologies. This research aims to examine the adopted trends of SMEs from Slovenia in the deployment of digital technology, the challenges they encounter, and the support they require in their digital evolution. Reacted firms mainly utilize traditional vehicles such as websites and teamwork platforms for online communication and presence. Nevertheless, utilization of such sophisticated digital tools as blockchain is still quite scarce because they are considered challenging to implement and applicable to a narrow range of industries. Variance analysis identifies differences in digitalization challenges between small, micro, and medium enterprises. Small companies confront greater financial constraints and require tailored support compared to larger SMEs, with a focus on improving employee digital competencies. While digitalization brings benefits like elevated processes and remote working, SMEs still struggle with differentiation and cultural changes.