We report two adult patients with varied urologic symptoms who were found to have inflammatory pseudotumor on histopathology. The first patient had a large, solid, enhancing retroperitoneal mass lesion and presented with increased frequency of urination and recurrent urinary tract infections. The second patient had an obstructing left distal ureteric stricture and presented with painless hematuria. Though preoperative radiological diagnosis of this entity is not feasible, the present article illustrates the imaging findings in this unusual disease entity with review of the relevant literature.