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Teacher attrition remains a major challenge in U.S. education, with 44% leaving within five years. Rural districts face added retention barriers such as isolation, low salaries, and limited professional growth. This study examines 15 years of administrative data from all 48 Wyoming school districts (n = 19,789 teachers; 10,698 exits) to identify attrition patterns and predictors. One- and five-year attrition rates were 9.9% and 32.2%. Mixed-effects logistic regression and Cox survival models revealed that University of Wyoming bachelor’s degree holders had higher retention, while special education staff had lower five-year retention odds. District-level variation significantly influenced separation risk. These findings underscore the need for localized, data-driven strategies—targeted hiring, mentorship, and professional development—to strengthen the rural teacher workforce.