<p>Skydivers are required to interpret person-context characteristics to overcome inherent internal challenges (i.e., fear and anxiety) and external challenges (i.e., equipment malfunctions) to successfully perform. Research suggests that as skydiving experience increases, skydivers' self-confidence in their actions increases, while their perception of risk and anxiety decreases. However, there is a lack of research investigating the influence of experience and considerations of performance in extreme sports. This study examined the influence of skydiving experience on the interpretation of risk perception, anxiety and self-confidence. Participants comprised 503 experienced Australian skydivers (<i>M_age</i> = 40.10, <i>SD_age</i> = 12.40; 79.5 % male). Using a mixed methods approach, skydivers completed measures of risk perceptions, anxiety, and self-confidence related to skydiving, as well as open-ended questions on their skydiving experiences. The findings indicated that increases in jumping experience led to greater self-confidence, and self-confidence mediated the relationship between all elements of jumping experience and cognitive and somatic anxiety associated with skydiving. Thematic analysis reinforced that skydivers understood the inherent risks associated with skydiving, and that skydivers adopted positive strategies that promoted self-confidence and mastery to perform successfully, while also managing their interpretations of risk and associated anxiety that potentially exists. Further research is needed to better understand the interpretation of person-context situations in extreme sports and recognize the important affordances for performance.</p>