This article examines Paul’s use of the term συστρατιώτης (“fellow soldier”) in Phil 2:25 and Phlm 2. Commentators have typically explained Paul’s two uses of the term, applied to Epaphroditus and Archippus, as either a synonym for “fellow worker”—applicable in theory to any fellow worker—or as specific applications of a more general Christians-as-soldiers metaphor prevalent throughout the canonical corpus of Pauline letters. In this article, I distinguish between the occurrences of military metaphors in Paul’s authentic and larger canonical corpuses, arguing that Paul’s authentic use of the metaphor is less common and more limited than the expansions of it in later canonical Pauline material. I then examine Paul’s limited use of “soldiering” metaphors and his specific use of συστρατιώτης alongside uses of the same metaphor and terminology in Greek and Roman moral-philosophical discourses and ancient letters. Against the common explanations of συστρατιώτης, I argue that Paul’s use of the term cannot be taken as indicating a general similarity between Christians and soldiers but, rather, is prompted in each case by distinctive elements in the circumstances of the person and relationship to which he applies the term and his broader rhetorical moves in the letters.