The COVID-19 pandemic imposed a large-scale adoption of teleworking in various fields, accepted by many employers as the ideal solution to protect their employees against the risk of contracting SARS-CoV-2. Working from home generated substantial savings for organisations and also contributed to alleviating employee stress. In addition to the potential positive effects, telework during COVID-19 favoured counterproductive behaviour, job insecurity, and intention to retire because of the negative outcomes generated by the growing conflict between personal life and working from home and professional and social isolation. The purpose of this research is to define and analyse a conceptual model capable of highlighting the way in which telework, job insecurity, and work–life conflict led to professional isolation and turnover intention, and finally, to the counterproductive behaviour of employees during the COVID-19 pandemic. This research was implemented using employees in Romania, an emerging European economy severely affected by the recent pandemic. The results have been analysed with the help of structural equations in SmartPLS, thus reflecting a significant influence of teleworking on work–life conflict, professional isolation, intentions, and insecurity during the pandemic. The insecurity of employees trained in teleworking contributes significantly to enhancing work–life conflict and professional isolation.