In recent years, small and medium enterprises worldwide have increasingly adopted digital technologies and cloud computing. The pace of this digital transition has varied across countries, and the socioeconomic conditions during the pandemic have further accelerated the digitalization of enterprises. This situation calls for an examination of the reasons, benefits, and risks associated with enterprises adopting cloud computing in different settings. Our study aimed to collect longitudinal data from 71 Montenegrin micro, small, and medium enterprises. We conducted a repeated measurement study with two measurement periods: 2017 and 2023. The quantitative results were analyzed alongside qualitative data from a semi-structured interview (N = 15) conducted in 2023. The findings revealed substantial shifts in SME attitudes towards cloud computing, highlighting key catalysts and influencing factors such as security, technological accessibility, external expertise, effort expectations, privacy, social influence, perceived security and safety, ease of use, and usefulness. These factors were examined in the context of global digital innovation, the impact of the COVID-19 pandemic, and recent cyberattacks that disrupted national e-services in Montenegro for 3–9 months. The findings provide new insights into how enterprises can become more prepared to effectively use cloud computing.
