Environmental scanning has become increasingly crucial for an organisation’s existence and a matter of interest for scholars and professionals. This research presents an outline of the situation in the field of multidimensional environmental scanning, focusing on Slovenian micro, small and medium sized organisations during the COVID-19 pandemic. Therefore, the paper aims to examine if top managers perceive the multidimensional (external) environment as uncertain and if there have been gender differences in multidimensional (external) environmental uncertainty perception during the COVID-19 pandemic. We researched the field of ecological, social, technological, economic, and political–legal environments. The nonparametric Mann–Whitney U test and descriptive statistics were used to test the research hypotheses. The results show that top managers are not aware enough of multidimensional environmental uncertainty. They do not perceive the ecological and social environment as unpredictable at all. Among the studied environments, they perceive the political–legal environment as most unpredictable. There are no statistically significant gender differences in perceptions of ecological, social, technological, economic, and political–legal environmental uncertainty. We suggest SME top managers pay more attention to environmental uncertainty and use environmental scanning methods to achieve more sustainable development.