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Historically, research examining graduate student socialization has attended to the structure of the socialization process, rather than how individuals interpret it. This qualitative study explored how 21 student affairs master’s degree candidates made sense of surprises that emerged during their initial socialization experiences. The findings suggest that participants encountered similar difficulties as they began graduate study; however, their responses to these challenges were influenced by their developmental capacity for self-authorship. Specifically, their approaches to the sensemaking process and their use of sensemaking resources (e.g., identity, social context) differed across their meaning making capacities.