We examine how online sociocultural context influences play experience in the popular online role‐playing game, World of Warcraft (WoW). We focus on how guilds, in‐game associations of like‐minded players, establish social relationships and cultural understandings that shape online play experience. Some guilds help their members regulate the stressful arousal emerging from challenging gaming activities—such as collaborative raids, where multiple players together try to defeat challenging opponents termed bosses—maximizing stress' positive eustressful potential. By contrast, so‐called “hard‐core” raiding guilds, the primary focus of this article, push their members to more extreme forms of online gaming, linking in‐game arousal with problematic patterns of play, potentially transforming pleasurable gaming eustress into harmful distress. Overall, we treat guilds as emergent communities of play, which, in the manner they differentially regulate their members’ gaming experiences, sharply illuminate the deep sociocultural shaping of the stress process. We suggest that these cultural processes are less visible in studies focusing more narrowly on distress or eustress alone—typically, medical anthropology in the first case, games studies in the second—making a balanced approach such as ours critical to psychological anthropologists hoping to clarify how culture lends psychobiological arousal its positive or negative valence.