Inguinoscrotal bladder herniation (IBH) is a rare type of inguinal hernia associated with significant urologic complications such as acute renal failure, hydronephrosis, obstructive uropathy, and sepsis. Diagnosis of this condition can be made with common imaging modalities including excretory urography, retrograde cystography, computed tomography (CT), and magnetic resonance imaging. We present the classic symptomatology and imaging findings of inguinoscrotal bladder herniation on CT urogram in two patients. Although the majority of IBH are diagnosed intraoperatively, radiologists and the surgical team should be aware of this diagnosis when working up a patient, as preoperative diagnosis is crucial to assist with surgical planning and avoid intraoperative complications. Level of evidence: 4.