The purpose of this study was to investigate the association between Chlamydia trachomatis reinfection rates of Puerto Rican adolescents and failure to follow the retesting protocol, failure of sexual partners to receive treatment, and failure to participate in the sexual orientation program about risk factors. Secondary data analysis, from a historical prospective study from the Health Department of Puerto Rico, was used in this study. Data analysis was restricted to adolescents 15 to 19-years-old who had a positive chlamydia result and reinfection pattern since January 2008 through December 2012. Multiple logistic regression analyses were run to predict Chlamydia trachomatis reinfection. Results showed a statistically significant association association between Chlamydia trachomatis reinfection and not having followed the retesting protocol (OR=1.243, 95% CI 1.089-2.930, p-value 0.038). A statistically significant association association was found between Chlamydia trachomatis reinfection and sexual partners having not received treatment (OR=1.713, 95% CI 0.761-2.024, p-value 0.029). A statistically significant association was found between Chlamydia trachomatis reinfection and having not participated in the Puerto Rico Department of Health's sexual orientation program (OR=1.243, 95% CI 0.762-2.026, p-value 0.034). The contribution to social change is identifying factors significantly associated with Chlamydia trachomatis reinfection. Study findings provide useful guidance for clinicians and public health professionals on how to reduce Chlamydia trachomatis reinfection rates among at risk Puerto Rican adolescents.