The ubiquitous nature and use of technology in contemporary societies continues to transform lives and work environments. At the same time, transport continues to be a major source of harmful emissions. Telework has been suggested as a means to reduce unnecessary work-related travel, including the daily commute. Telework occurs when Information Communication Technologies (ICTs) are applied to enable work be accomplished at a distance from the location where results are needed. However, despite its promising nature and early optimist predictions, telework has largely failed to capture management and workers' attention and imagination. Using a multi-level perspective (MLP) on sociotechnical transitions approach, this study reveals why telework continues to remain a ‘niche’ practice dominated by a small set of industries, managers and workers. The paper builds on MLP thinking with a view to highlighting behavioural, cultural, and political aspects of socio-technical transitions and their interactions, which are frequently limited in classical MLP thinking. The failure to enrol additional niche-actors, the dominance of traditional forms of working and automobility, and the absence of policy and lack of legitimacy, all act negatively to keep telework from emerging from the niche to the regime level and becoming established as a more mainstream practice.