Introduction: Criteria for starting weight-bearing on the heel with a symptomatic calcaneal insufficiency fracture have not yet been reported. Case Presentation: We describe a rare case of a 52-year-old woman with a calcaneal insufficiency fracture who sustained a second ipsilateral calcaneal insufficiency fracture within a short time span. The initial fracture was not evident radiographically, but was detected using magnetic resonance imaging (MRI). The patient rejected our advice to avoid weight-bearing on the heel, instead opting to use a silicone heel orthosis. Although there were no abnormal local findings, the stand on heel test was positive at each subsequent visit until 2 months after her first medical examination. At this time, radiographs showed a sclerotic line; however, a second round of MRI showed a new calcaneal insufficiency fracture anterior to the initial calcaneal insufficiency fracture. The patient then agreed to stop weight-bearing on the heel. Three months after the initial visit, radiographs showed two sclerotic lines, and the stand on heel test became negative for the first time; hence, weight-bearing was permitted. There was radiographic evidence of fracture healing and complete resolution of symptoms 4 months after the initial visit. Conclusions: The callus formation seen on radiographs is helpful in determining when to start weight-bearing; however, fresh insufficiency fractures of the ipsilateral calcaneus may not be detected by radiography. Since local findings such as tenderness, swelling, and heat are subjective, the criteria for starting weight-bearing on the affected heel with an insufficiency fracture should be based on not only radiographs but also objective clinical findings such as the stand on heel test.