It is well-known that communication with patients can be challenging for residents. Although some studies have focused on residents’ experiences of communication challenges, few, if any, have investigated the language residents use when describing such challenges. In this study, we explore the metaphors residents use when asked to share stories about challenging communication situations. Metaphor has been the focus of research in a variety of health-related disciplines; here, we use it to gain an understanding of why these situations are seen as challenging. Methodologically, we draw on metaphor-led discourse analysis, which facilitates a systematic approach to the identification and analysis of metaphors. The empirical material consists of 138 Danish residents’ 259 narratives about communication challenges. We identified more than 700 metaphors used in connection with accounting for communication challenges with patients. The metaphors are primarily driven by vehicles belonging to four groups, namely: “Location,” “Movement,” “Games and play,” and “Battle and warfare.” We discuss the implications of these metaphors in relation to residents’ conceptualizations of communication and challenges.