Telework is increasingly becoming more prevalent over the last few decades. Mandatory teleworking is an unforeseeable side-effect of the recent pandemic. Managers and employees are inexperienced in handing large scale adoption of telework. The challenges of these implementations need to be explored in detail to develop counter-strategies. The study collected data from 231 managers across industries on these challenges and their effects through an online survey. These managers are part of active teleworking teams. We find that the challenges present by the large-scale mandatory telework affect employees’ perceived autonomy, which subsequently increases the work monotonicity. This has an adverse effect on the work engagement of employees in organizations. A framework detailing the challenges and its outcomes has been presented and empirically tested as part of this research initiative.