Despite the rapid entrance of women into the workforce over the past several decades, many workplace experiences unique to women remain poorly understood. One critical, yet understudied, area is the intersection of work and pregnancy. Because pregnancy remains concealable for a substantial amount of time, expectant employees must navigate decisions regarding to whom, when, and how to disclose their pregnant identities at work. In light of evidence that has suggested pregnancy is often stigmatized within the workplace, I employed a retrospective longitudinal design to explore the extent to which women’s expectations about discrimination—anticipated discrimination—shape their pregnancy disclosure behaviors, and the extent to which these different behavioral strategies are associated with higher or lower experienced discrimination. I also examined the link between pregnancy disclosure strategies and psychological distress. Taken together, findings suggest that pregnant employees’ expectations about pregnancy discrimination play a role in shaping disclosure behaviors at work. Furthermore, certain behavioral strategies for pregnancy disclosure were linked with average reports of experienced discrimination and momentary reports of psychological distress. I also discuss theoretical and practical implications.