Anatomical disruption of the ureter is a rare phenomenon that alters the positioning of the ureter within the abdominal or pelvic cavity. It is even rarer for ureteral presence to be located within inguinal hernias, especially bilaterally. We explore a case of a 76-year-old male with bilateral inguinal hernias, each containing a portion of the ureter from its respective kidney. The patient initially presented to the internal medicine service with hematochezia secondary to diverticulitis and was largely asymptomatic from the perspective of genitourinary function. The patient’s presenting condition was resolved with appropriate antibiotic treatment, and the ureteral findings were used for patient counseling and education on the risks of future hernia surgery, should the patient need it. This report will present the relevant imaging findings that highlight the anatomy in question, as well as discuss possible etiologies associated with this anatomical finding. We will also explore the risks that pose a threat to ureters within an inguinal hernia and highlight the importance of thorough preoperative and intraoperative guidance and visualization to ensure no ureteral damage has occurred. This case serves as an example of the potential risks to be aware of prior to performing a routine surgical procedure and highlights a potential need for more reliability and comfort with medical imaging modalities.