This chapter looks into two paradoxes of the post-Soviet Russian gender order and post-Soviet Russian masculinities. The first paradox is a large-scale, well-documented structural contradiction which has persisted throughout the entire post-Soviet period of Russian history: despite the fact that military service remains a constitutional duty of male citizens in Russia, only a minority of men in the draft pool end up serving in the armed forces. The second paradox, commonly known but underexplored, relates to the symbolic dimensions of gender relations in Russia. I addressed this issue in my relatively small-scale qualitative research project on contemporary Russian masculinities: I found that despite harsh criticism of the contemporary Russian army and personal unwillingness to serve in the military, only a small number of the research participants expressed consistent antimilitary sentiments and/or considered military service as unnecessary and pointless. My research also showed that the military and militarism remain a crucially important gendered terrain on which Russian masculinities are contested and achieved. This is evident even in the context of a severe crisis of the national military and even for men who have no experience of military service.