The deltoid ligament is vitally important in the stability of the ankle and preventing excessive medial ankle movement. Historically, the impact of medial ankle instability has not been well understood in the setting of chronic ankle instability. A retrospective review of 226 patients treated for ankle instability between 2017 and 2022 identified 40 patients who required both medial and lateral repair. Decision for medial deltoid repair was based upon patient presentation, MRI findings, intraoperative fluoroscopy and final confirmation via arthroscopic positive "drive-through sign". Preoperative and postoperative American Orthopedic Foot and Ankle Society (AOFAS) hindfoot-ankle scores, Patient-Recorded Outcomes Measurement Information System (PROMIS) scores, and Karlsson-Peterson Ankle Function (K&P) scores were obtained and compared. There were statistically significant improvements found in all 3 scoring systems at a mean follow-up time of 11.7 months postoperatively. In the setting of chronic ankle instability, consideration should be given to the evaluation and potential repair of the deltoid ligament in order to provide sufficient stability to the medial ankle.