Abstract: Background: Chlamydia trachomatis (CT) and Neisseria gonorrhoeae (NG) are highly prevalent sexually transmitted infections (STIs) with significant negative impacts on military readiness. Reinfections are common, and identifying risk factors can inform risk-based screening strategies. This study investigated factors associated with chlamydia and gonorrhea reinfections within six months following an initial infection among United States Army soldiers at Fort Bragg. Methods: Soldiers diagnosed with CT or NG were followed for six months with visits at 2, 3, 4, or 5 months and a final visit at 6 months. Reinfections were defined as positive CT or NG tests or self-reported diagnoses at study visits or through chart review. A recurrent events model was used to analyze associations between reinfections and sexual practices, travel, and self-reported symptoms. Results: Among 275 (79%) of the 347 enrolled participants who completed at least one follow-up visit >30 days post-treatment, 63 (23%) experienced at least one reinfection. Having symptoms since the last visit (adjusted hazard ratio [aHR], 95% confidence interval [CI]: 3.62, 2.12–6.18) and having two or more partners (aHR, 95% CI: 2.00, 1.13–3.52) since the last visit were significantly associated with a higher risk of reinfection compared to no symptoms and one partner, respectively. Conclusions: This study identified experiencing symptoms and having multiple recent sexual partners as factors associated with chlamydia and gonorrhea reinfections. These findings can inform risk-based screening strategies to improve military health and readiness. Future research with longer follow-up is needed to further explore the association between reinfections and recent sexual practices and travel.