Phlegmasia cerulea dolens (PCD) is a rare and severe form of deep vein thrombosis (DVT) associated with limb ischemia. We present the case of a 21-year-old female patient who presented with lower extremity numbness, pain, and swelling, accompanied by pleuritic chest pain and shortness of breath. She had a recent history of receiving a Depo-Provera shot for birth control. Diagnostic assessments revealed an extensive femoral-to-popliteal DVT and bilateral pulmonary embolisms. The patient underwent a series of interventions, including thrombectomy, catheter-directed thrombolysis, and repeat thrombectomy with venoplasty. She was discharged on anticoagulation therapy and showed favorable outcomes during her hospital stay. This case highlights the potential association between Depo-Provera use and the development of PCD, emphasizing the importance of prompt diagnosis, multidisciplinary management, and follow-up care.