An injury during deployment disrupts family and life functioning. The purpose of the present study was to provide an in-depth examination of three injured National Guard soldiers showing how differential experiences of navigating multiple systems to obtain treatment for injury resulted in different adjustment trajectories for these soldiers and their families. A comparative case study examined three families where a soldier’s injury was a central theme of family adjustment. Qualitative data were drawn from interviews conducted conjointly with both the soldier and spouse to provide an in-depth perspective of adjustment, meaning, and resource utilization patterns. In addition, survey data were collected at three time points in the deployment cycle (predeployment, 90 days post, and 1 year). These data were integrated into the case analysis, including mental health, marital relationship, treatment history, and characteristics of resilience. Study findings suggest that a delay in diagnosis, wait time for treatment, and the lack of comprehensive formal and financial support for a soldier following nonhostile injury lead to a pileup of stressors that are detrimental to the soldier’s physical and mental health, financial stability, and family well-being. Further study is needed to understand how these system level issues impede resilience among National Guard families.