This field report describes an investigation to identify cases to control a syphilis outbreak in a prison and determine whether clinical, case management, and surveillance practices influenced the outbreak occurrence, detection, or management. Key performance measures were assessed to evaluate timeliness and quality of clinical and case management activities and surveillance practices. Thirty cases were found. Prior to the investigation, median times for clinical and reporting/surveillance measures were 15 days from primary and secondary (P&S) symptom onset to exam, 7 days from P&S exam to treatment, and 63 days from serologic test to the State's receipt of case. After the investigation, these measures improved to 8, 4.5, and 28 days, respectively. Lack of adherence to surveillance and clinical management protocols likely contributed to this outbreak, which was curtailed by aggressive control measures. Abstract published by arrangement with Sage Journals.