ABSTRACT Objectives Approximately 70% of the military personnel experience chronic sleep insufficiency, which negatively impacts military readiness and health. Military sleep health does not appear to be improving despite targeted programs to optimize sleep. The present quasi-experimental study aims to evaluate a single-session sleep intervention in United States Air Force (USAF) Technical Training. Method A group-based Brief Sleep Intervention (BSI) was developed for the target population. Participants included 321 technical school students (Mean age = 21; 82% male; 67% White) who were assigned to the BSI (n = 203) or a control group (n = 118). Propensity-score-weighted multivariable logistic regression was employed to compare outcomes. Results At the 2-week follow-up, students in the BSI were significantly more likely to report sleeping 6 or more hours on weekdays (OR = 1.49, p < .001) and “Good/Very Good” sleep quality (OR = 1.50, p = .032) than those in the control group. In addition, 69.2% of the students in BSI reported having engaged in the self-selected “Action Step” chosen during the intervention. Conclusions To our knowledge, this is the first study to test a preventative sleep intervention in USAF Technical Training. Results suggest that a single-session group intervention can promote behavioral changes and improve sleep health.