The occupation of police has been contended as one of the most stressful across the globe. With the rise in the experience of work stress and strain among police, their personal and organizational wellbeing is at maximal threat. Thus, this study aimed to explore the process through which job demands (challenge and hindrance stressors) can influence positive work outcomes which included work engagement and thriving at work. Drawing from the Positive Psychology framework, such as Seligman’s concept of Flourish and the PERMA model (2011), this study investigated a moderated-mediation model to test the role of ‘meaningfulness at work’ in explaining the relationship between job demands and positive work outcomes. It was further proposed that this indirect effect will be conditioned on police personnel’s level of optimism. Employing a purposive sampling technique, 352 police personnel of varying ranks across 195 police stations in India participated in the study. The results of this study revealed that meaningfulness at work significantly explained the positive influence of challenge stressors on work-related outcomes under high levels of optimism. However, this was found to be significant only for personnel who belonged to the lower and middle ranks and not for those in higher ranks.