Although there is ample evidence that endorsement of traditional masculinity ideology may negatively affect veteran men’s military to civilian transition, it remains unclear which specific facets of traditional masculinity are most likely to impede successful transition to civilian life. To better understand the association between traditional masculinity ideology and veteran transition, this study sought to examine the relationship between five facets of traditional masculinity ideology (restrictive emotionality, avoidance of femininity, toughness, dominance, and self-reliance) and four factors associated with difficult veteran transition (posttraumatic stress disorder [PTSD], depression, perceived social support, and alcohol-related problems) in ( N = 289) veteran men. Results indicate that restrictive emotionality was the most significant contributing facet of traditional masculinity ideology to PTSD, depression, and perceived social support, whereas avoidance of femininity was the masculinity facet most significantly associated with alcohol-related problems. Theoretical and clinical implications are discussed.