Growing evidence suggests that work breaks in greenspace may promote the well-being of knowledge-sector workers, yet understanding of person–environment interactions in relation to the outdoor setting of workplaces is underdeveloped. This study investigated relationships between individual factors and both employees’ use of workplace greenspace and the restoration outcomes they experienced from outdoor work breaks, through a questionnaire survey (N = 366) of employees at five urban-fringe science park business sites. A series of regression models suggested that job stress was positively related to levels of greenspace use and restoration benefits; however, the restoration reported by users varied depending on the social context of use. At the same time, key groups less engaged with the greenspace were identified. Finally, the analysis suggests that although some work-related factors may influence person–environment interactions in this context, individuals’ relationship with greenspace appears to transcend the domains of work and home/leisure to a large degree.