This paper tests the relationship between organizational expectations to monitor work-related electronic communication during nonwork hours and the health and relationship satisfaction of employees and their significant others. We integrate resource-based theories with research on interruptions to position organizational expectations for e-mail monitoring (OEEM) during nonwork time as a psychological stressor that elicits anxiety due to employee attention allocation conflict. E-mail–triggered anxiety, in turn, negatively affects the health and relationship quality of employees and their significant others. We conducted three studies to test our propositions. Using the experience sampling method with 108 working U.S. adults, Study 1 established within-employee effects of OEEM on anxiety, employee health, and relationship conflict. Study 2 used a sample of 138 dyads of full-time employees and their significant others to replicate detrimental health and relationship effects of OEEM through anxiety. It also showed crossover effects of OEEM on partner health and relationship satisfaction. Finally, Study 3 employed a two-wave data collection method with an online sample of 162 U.S. working adults to provide additional support for the OEEM construct as a distinct and reliable job stressor and replicated findings from Studies 1 and 2. Taken together, our research extends the literature on work-related electronic communication at the interface of work and nonwork boundaries, deepening our understanding of the impact of OEEM on employees and their families’ health and well-being.