The aim of this analysis is to provide an overview of the legal regulation of teleworking in Montenegro, with a view to analysing the available space in the legal framework for the application of teleworking. Because of teachers’ peculiar position during the pandemic, a special section describes the key challenges they have faced, according to the interview conducted with the respective trade union. A series of recommendations is provided concerning the existing entry-points and the changes needed in the legal framework, as well as the potential to improve teleworking practices.