Employees want to be able to telework and organisations want to provide the ideal environment to make it a success story. While some teleworkers experience telework success, that is, are satisfied and perform well, others do not. To understand the drivers of successful and unsuccessful telework, we used a mixed methods approach, taking a stress-theoretic and configurational perspective. In Study 1, we conducted a quantitative analysis of data collected in a survey of 375 teleworkers to identify configurations of information and communication technology (ICT), work and family related challenge and hindrance stressors that lead to high and low telework success. In Study 2, we analysed qualitative data collected in interviews with 52 teleworkers to shed light on the interplay among ICT, work and family related challenge and hindrance stressors in the configurations that lead to high and low telework success. We contribute to telework research by showing that high and low telework success results from configurations of ICT, work and family related challenge and hindrance stressors. We extend the literature by showing that teleworkers benefit from challenge stressors only when they do not experience hindrance stressors. Methodologically, we provide a blueprint for an innovative approach using deductive fsQCA to refine, extend and delimit theory.