Calcific insertional Achilles tendinopathy (CIAT) is a relatively common musculoskeletal entity that results in significant pain and disability, as well as posterior muscle group weakness. There is a lack of evidence criteria to support the timing of operative intervention, choice of procedures, or whether equinus requires treatment. The purpose of this study was to retrospectively review 45 patients (48 feet) who have undergone surgical management of CIAT with concomitant posterior muscle group weakness with the single heel rise testing. All patients underwent debridement and repair of the Achilles tendon with reattachment of the Achilles tendon to the calcaneus, ostectomy of the calcaneus, and flexor hallucis longus tendon transfer. Those patients with equinus also underwent gastrocnemius recession. The focus includes patient-reported satisfaction, time to return to normal shoe gear, and the incidence of revision surgery. The overall average of time to weightbearing was 4.3 weeks. After surgery, 73.3% (n = 33) of the 45 patients responded to the following question: “Would you have this surgery done again?” Of these patients, 93.9% (n = 31) responded “Yes” and 6.1% (n = 2) responded “Unsure.” Of the same 33 patients, 84.8% (n = 28) responded that they were “Very Satisfied” with the procedure and 15.2% (n = 5) responded that they were “Satisfied.” Twelve patients (26.7%) did not respond to either question. One of the 12 patients (8.3%) who did not respond had bilateral procedures. None of the patients experienced tendon rupture, deep vein thrombosis, or the need for revision surgery. Four patients (8%) experienced a superficial infection, whereas 1 patient (2%) had development of a deep infection. No correlations were found when looking at the relationship between body mass index and return to weightbearing/normal shoe gear with Spearman analysis.