Study Objectives: Examine the relationship between self-reported sleep parameters and indicators of resilience in a US military population (n = 55,021). Methods: Longitudinal analyses (2001-2008) were conducted using subjective data collected from Millennium Cohort Study questionnaires and objective data from military records that included demographics, military health, and deployment information. Subjective sleep duration and insomnia symptoms were collected on the study questionnaire. Resilience metrics included lost work days, self-rated health, deployment, frequency and duration of health care utilization, and early discharge from the military. Generalized estimating equations and survival analyses were adjusted for demographic, military, behavioral, and health covariates in all models. Results: The presence of insomnia symptoms was significantly associated with lower self-rated health, more lost work days, lower odds of deployment, higher odds of early discharge from military service early, and more health care utilization. Those self-reporting8 h (long sleepers) of sleep per night had similar findings, except for the deployment outcome in which those with the shortest sleep were more likely to deploy. Conclusions: Poor sleep is a detriment to service members' health and readiness. Leadership should redouble efforts to emphasize the importance of healthy sleep among military service members, and future research should focus on the efficacy of interventions to promote healthy sleep and resilience in this population.