Multiple deployments are common among military personnel who served in Operation Enduring Freedom and Operation Iraqi Freedom and are associated with greater posttraumatic stress symptoms (PTSS). Homefront stressors (i.e., family, occupational problems) resulting from deployments may increase the risk of PTSS. Moreover, with multiple deployments, a new deployment may occur while still experiencing homefront stressors from previous tours. This prospective study assessed whether homefront stressors from a previous tour increased the risk of PTSS after a new deployment. It also examined the effects of homefront stressors at postdeployment. Survey data were obtained from U.S. National Guard soldiers with previous deployments prior to (Wave 1) and after (Wave 2) a new deployment to Iraq (N = 196). Homefront stressors reported at Wave 1 (β = .154, p = .015) and Wave 2 (β = .214, p = .002) were both significantly predictive of PTSS at postdeployment, even after adjusting for warzone stressors, predeployment PTSS, and other variables. A pattern of chronic homefront stressors (i.e., homefront stressors at pre‐ and postdeployment) was associated with higher levels of PTSS at postdeployment (β = .220, p = .002). Service members with multiple deployments are at greater risk for PTSS if deployed with homefront stressors from previous tours and/or face these stressors at postdeployment.