The main idea of this research is to examine how teleworking has affected employee perceptions of organizational efficiency and cybersecurity before and during the COVID-19 pandemic. The research is based on an analytical and empirical approach. The starting point of the research is a critical and comprehensive analysis of the relevant literature regarding the efficiency of organizations due to teleworking, digital information security, and cyber risk management. The quantitative approach is based on designing a structural equation model (SEM) on a sample of 1101 respondents from the category of employees in Montenegro. Within the model, we examine simultaneously the impact of their perceptions on the risks of teleworking, changes in cyber-attacks during teleworking, organizations’ capacity to respond to cyber-attacks, key challenges in achieving an adequate response to cyber-attacks, as well as perceptions of key challenges related to cybersecurity. The empirical aspects of our study involve constructing latent variables that correspond to different elements of employee perception; namely, their perception of organizational efficiency and the extent to which the digital information security of their organizations has been threatened during teleworking during the pandemic.