Introduction and Importance Long-term mechanical complications after inferior vena cava (IVC) filter placement include embedded or tilted filters, erosion of the vena cava, filter thrombosis. In the setting of caval thrombosis, patients may subsequently develop venous hypertension and post-thrombotic syndrome (PTS). Here we present three unique cases of IVC filter complications and surgical management. Case Presentation A 30-year-old female presented with acute abdominal pain, revealing a duodenal perforation caused by an IVC filter eroding into her duodenum. A 42-year-old female with an IVC filter in place for 20 years due to a prior pulmonary embolism underwent laser-assisted retrieval of the filter due to concerns of caval adherence. A 48-year-old male with a history of DVT, venous stasis ulcer, and an IVC filter presented for filter retrieval. Clinical Findings and Investigations The surgical techniques described in this report include complicated IVC filter retrieval, performed in cases of filter complications including migration, fracture, duodenal perforation and IVC thrombosis resulting in PTS. One case, requiring open retrieval, is explained and the surgical technique is provided. There are images and videos of these procedures to enrich the learning experience. Intervention and Outcomes The surgical techniques described in this report include complicated inferior vena cava filter retrieval, performed in cases of filter complications including migration, fracture, duodenal perforation and IVC thrombosis. One case, requiring open retrieval, is explained and the surgical technique is provided. There are images and videos of these procedures to enrich the learning experience. Relevance and Impact Endovascular retrieval of long-term complicated IVC filters is challenging, but it can be a safely performed in many patients. However, open surgery may be necessary in selected patients.