Guided by the transactional theory of stress and coping, this study documents and examines how journalists in Singapore experienced covering the COVID-19 pandemic. Through an interview with 22 journalists, this study finds a variation in how journalists experienced covering the crisis, and how changes in their work routines shaped such experiences. Forced to work from home, many journalists experienced a blurring of work and home boundaries. An important determinant of their experience is how well they were are able to cope, and the interviewees underscored the importance of organizational support in their coping process. These experiences and coping processes, however, were also shaped by their work status. While those working for mainstream organizations received sufficient support, freelancers and those affiliated with small media startups had a different experience, as COVID-19 magnified pre-existing disparities among journalists.