Transport continues to be a significant user of energy and a major source of Greenhouse Gases (GHGs) emissions worldwide. Moreover, the ubiquitous nature and use of technology in contemporary societies continues to transform lives and work environments. Telework occurs when Information Communication Technologies (ICTs) are applied to enable work be performed at a distance from the location where the results are needed, or where work would traditionally have been accomplished in the past. An essential feature of the Smarter Travel initiative, telework has been suggested as the means of reducing or eliminating unnecessary travel in the form of the daily commute to and from work, and a positive approach to reducing the overall consumption of distance in Ireland. As an innovative way of working, telework, however, has largely failed to capture management and workers’ attention and imagination despite early optimist predictions and forecasts. It remains a marginal practice and its social and environmental impacts and consequences remain somewhat ambiguous. Using a multi-level perspective (MLP) on sustainability transitions framework, this paper considers telework as a sociotechnical practice and attempts to reveal why it continues to remain a ‘niche’ practice dominated by specific worker and management profile and industries. What conditions, barriers and pressures impact upon the development and spread of this method of working across various industries and workforces? This study finds that a failure to enrol additional niche-actors, the dominance of traditional ways of working, and a lack of legitimacy in terms of policy, governance and management, have acted negatively to keep telework from emerging from a niche to the regime level, or becoming established as a more mainstream practice and method of working. Telework appears destined to fail even before it has been given a chance to shine as an economic, social and environmental means of sustainability, and transport policy initiative.