Not uncommonly, hostile prison environments can lead desperate prisoners to place foreign materials into natural orifices in an effort to gain transfer to an outside healthcare facility. In this article, we present a case series of urethral foreign body insertion of varying burdens and durations requiring transfer to our facility for surgical management. Endoscopic retrieval was the initial management in each case; one case required conversion to open cystotomy for complete removal due the orientation, amount of inserted foreign body, and erosion into the proximal urethral and bladder urothelium.