Background/Objectives: Calcinosis cutis (CC) is a condition that may develop in the course of several autoimmune connective tissue diseases (ACTDs). Among these, the conditions most frequently associated with CC are systemic sclerosis (SSc) and dermatomyositis (DM). Despite both the prevalence and diversity of available treatment options, therapeutic recommendations remain not fully established due to a limited number of studies and lack of unambiguous evidence regarding their effectiveness. Case Presentation: We report two cases of patients with DM and concomitant massive cutaneous calcifications who were treated: in the case of a 71-year-old man with DM and past medical history of primary cutaneous T-cell lymphoma (CTCL) who received intralesional (IL) 25% sodium thiosulfate (STS) with platelet-rich plasma (PRP) injections, and, in the case of a second patient, 24-year-old woman with nephrolithiasis, who received intravenous immunoglobulin (IVIG) infusions at a dose of 2 g/kg in combination with prednisone at a dose of 5 mg/day. Conclusions: The applied treatment led to reduction in pain, size, and number of calcified lesions. Additionally, healing of fingertip ulcers after PRP injections was observed. While this report highlights only two isolated cases, the use of IVIG and STS with PRP injections appears to be an effective treatment method. Nevertheless, both standardization and additional research are required.