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Ureterosciatic herniation is a rare cause of ureteral obstruction. A bilateral presentation is especially uncommon. We present a female patient in her late 80s diagnosed with bilateral ureterosciatic herniation. She presented with 24 hours of severe left flank and suprapubic pain. A CT scan of the abdomen/pelvis revealed moderate to severe left-sided hydronephrosis and hydroureter, and a laterally coursing distal left ureter. Retrograde pyelograms revealed bilateral ‘curlicue sign’ pathognomonic for ureterosciatic herniation with left-sided hydronephrosis. Management required left percutaneous nephrostomy (PCN), which was later converted to percutaneous nephroureteral stent (PCNU). The patient elected for routine left PCNU exchanges every 3 months. Bilateral ureterosciatic herniation is an exceptionally rare cause of ureteral obstruction. Retrograde pyelograms are diagnostic. Initial management achieves renal decompression and hernia reduction with a ureteral stent or PCN/PCNU. Surgical correction offers definitive repair. For patients not amenable to surgery or ureteral stent exchanges, routine PCNU exchanges are a reasonable approach for management.