Against the backdrop of World War II, the so-called preparedness literature was developed in Sweden. This literature, written by both female and male authors, in poetry and prose, engaged with the war in solidarity with Sweden’s attacked and occupied neighbors, Finland, Norway, and Denmark as well as the national scenario of military preparedness. In this article, novels by Helmer Linderholm and Peter Nisser, portraying military masculinities, are in focus. They are taking place in border regions (Sweden-Finland and Sweden-Norway) and in Finland. The soldier characters can be divided into two groups: the conscripted Swedish soldiers pictured by Linderholm and the (volunteering) soldiers at the Finnish front described by Nisser. The article argues that there is a wide range of masculinities on display in these novels, from the one with pacifist inclinations and doubts about war at large to the one considering killing the (dehumanized) enemy a self-evident and even satisfactory activity. The military masculinities are also discussed in relation to female characters that the soldiers encounter. The overarching patriarchal order at war and conflict is disclosed by the fact that the women in the novels, with a few exceptions, are treated in a demeaning manner and exposed to sexual harassment and violence by the soldiers. Subjects such as (anti)violence, nation(alism), heteronormativity, race, and class are analyzed by drawing from research and theories on masculinities at war (Showalter 1987; Eduards 2007; Young 2007; Ahlbäck and Kivimäki 2008; Kronsell 2012; Ahlbäck 2014; Järvstad 2022).