Pregnancy loss is often stigmatized and is considered to be a taboo topic in the workplace, causing employees to suffer in silence. Yet, pregnancy loss is unequivocally a workplace issue – it can occur at work and influence work outcomes, such as performance, job attitudes, and employee wellbeing. Unfortunately, there is little research examining the intersection between work and pregnancy loss, leaving employers with little evidence-based guidance on how to support employees during and after pregnancy loss. The purpose of this qualitative study of working women (N = 29) is to provide insight into the ways by which work influences, and is influenced by, employees' physical and psychological experiences of loss. We utilized a phenomenological approach which revealed 12 themes that were temporal in nature and represented the interconnectedness of work and pregnancy loss. Themes related to the pre-loss experience (pregnancy experiences), loss experience (healthcare; physical health; psychological health; partner's experiences; loss disclosure; memorialization), short-term post-loss experience (work leave; workplace support; stigma), and long-term post-loss experience (return-to-work; shifts in perspective and identity). These results revealed that pregnancy loss experiences unfold over extended periods of time and across domains, involving the interaction between work, family, and healthcare systems. Findings are interpreted through the lens of bioecological systems theory and boundary theory, and illustrate the criticality of supportive workplace practices, such as return-to-work accommodations, bereavement support, and leave options, in supporting employee health and work outcomes.