The elevated risk of thromboembolism (TE) in association with inflammatory bowel disease (IBD) is well-established in literature. Herein, we present a case of a 70-year-old patient with steroid-dependent ulcerative colitis who presented with exertional dyspnea and abdominal pain. Investigations revealed extensive bilateral iliac and renal and caval venous thrombosis as well as pulmonary emboli. In addition to the rarity of such a finding in this location, this case serves to remind clinicians of the elevated risk of TE in those with IBD, even among those with IBD that has been in remission, especially in those presenting with unexplained abdominal pain and/or renal injury. TE can be life-threatening and requires a high index of clinical suspicion to establish early diagnosis and prevent propagation.