Teleworking increased during the COVID-19 pandemic and continues to be a major working practice at a higher rate than before the pandemic. Over the past three years, employees have engaged in various forms, types, and extents of telework. Experiences with telework have had both positive and negative effects on employees’ well-being. Personality traits also appear to play a significant role in employee engagement in a telework environment (Clark et al., 2012). In addition, another important factor, gratitude, is considered to be a crucial predictor of positive subjective well-being (SWB) in the work context (Datu et al., 2022). To this end, the present study examined the relationship between Big Five personality traits and teleworkers’ well-being as well as their direct and indirect effects on gratitude. To examine possible predictors, 230 teleworkers completed an online questionnaire. A path analysis was conducted to test the relationships among variables. The results show that different personality types may influence employees’ attitudes toward telework and could play an important role in determining subjective well-being in teleworking. Specifically, conscientiousness, extraversion, and agreeableness were found to be correlated with a positive and statistically significant impact of positive feelings toward telework, whereas neuroticism was associated with lower well-being toward telework.