Although menstrual pain (dysmenorrhea) is common and can have detrimental effects on workability and social functioning, little is known about how people manage dysmenorrhea in their professional life. Existing evidence indicates that people with dysmenorrhea often engage in presenteeism, meaning they work despite experiencing symptoms and report perceptions of social stigma around menstruation. In this study, we investigated individual health-related factors, psychosocial factors, and work factors associated with period pain presenteeism in a cross-sectional survey study including N = 668 employed people with experiences of dysmenorrhea. Our results show that symptom severity, disclosure of menstrual pain to the leader, and remote work are directly associated with period pain presenteeism. Also, we found that disclosure to the leader was associated with leader gender, leader-member exchange (LMX), and the absence of a medical diagnosis, indicating a potential mediating effect. We did not, however, find the perceptions of public beliefs regarding the concealment of menstruation to be related to presenteeism or disclosure. Our findings have important implications for theory building and research on menstruation in occupational contexts, occupational health management and communication, diversity management in organizations, and leadership training.