This article examines the intersection between masculinity, military culture, and hospice and palliative care (HPC). The authors conducted a narrative literature review, supplemented with clinical annotations, to identify the impact of masculinity and military culture on the following topics salient to end-of-life care with older male veterans: pain management, mental health, coping, communication, autonomy and respect, and family roles. Findings suggest that traits associated with masculinity and military culture have an influence on the end-of-life process and HPC for older male veterans. Specifically, results suggest that older male veterans may deny or minimize physical pain, decline mental health treatment, utilize maladaptive coping strategies, avoid emotional conversations, struggle to manage perceived shifts in autonomy, and experience challenges negotiating changing family roles. The authors provide clinical recommendations for providers across various disciplines to address the aforementioned concerns with older male veterans in HPC. Overall, information presented in this article may be an important contribution to the literature for building cultural competencies with older male veterans and has the potential to improve the delivery of HPC for veterans and their families.