Insertional Achilles tendinopathy (IAT) is a common condition causing pain and dysfunction. Patients with diabetes, hyperlipidemia, hypothyroidism, and obesity are at increased risk of developing IAT. These comorbidities also carry an increased risk of wound healing complications following surgery. Therefore, there is a need for alternative management strategies for this high-risk patient population. This study investigated the potential role of isolated GR in patients with chronic IAT. This study is a single-institution retrospective review of adult patients who underwent isolated GR to address chronic IAT with a minimum 1-year follow-up. Demographics, complications, radiographic findings, and preoperative and postoperative patient-reported outcome scores (PROs) were collected. The primary outcome was improvement in PROMIS scores from preoperative to postoperative. Secondary outcomes were complication and reoperation rates. Sixteen patients underwent open GR with a mean follow-up of 2.7 years. Postoperative PROMIS domain scores improved significantly from preoperative scores for physical function, pain interference, pain intensity, and global physical function. Two patients (13%) underwent reoperation (open calcaneal exostectomy and tendon debridement) at a mean time of 7 months from gastrocnemius recession. One patient developed a postoperative hematoma that resolved with conservative management. This single-institution series reports on a small cohort of patients with chronic IAT treated with open GR. We found significant improvement in patient-reported outcomes. Rates of complication and reoperation were low. This study supports the potential use of isolated gastrocnemius recession in IAT patients who, because of age or medical comorbidities, may benefit from a less invasive surgery and faster rehabilitation. Level III, retrospective case control study.