Most people deal with a death loss without needing clinical help. However, researchers agree that for about 10-12% of individuals who experience a death loss, grief symptoms become chronic, and more severe. Chronic, severe grief symptoms are otherwise known as complicated grief. Military service members experience a myriad of factors that likely increase their risk of developing complicated grief, yet few studies have examined grief within military populations. The aim of the current study was to address the lack of grief research in the military psychology literature and provide practitioners who treat military service members with a deeper understanding of the role of meaning in the development of complicated grief, using attachment theory and meaning making model as a guide. It was hypothesized that insecure attachment and perceived closeness would be positively associated with complicated grief, meanings made would be negatively associated with complicated grief, meanings made would mediate the relationship between insecure attachment and complicated grief, and that meanings made would mediate the relationship between perceived closeness and complicated grief. Two hundred thirty-eight military service members were surveyed and data were analyzed using path analysis. Results suggested insecure attachment and closeness were positively associated with complicated grief and meanings made were negatively associated with complicated grief. Mediation was supported. Implications for theory, research and practice are discussed.