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Ileal conduit-vaginal fistulas are a rare but challenging complication of urinary diversion. Here we identify risk factors and summarize the workup and conservative management strategies for this complication. We present two cases of elderly women with remote history of cancer who presented with persistent urinary leakage from the vagina several years after ileal conduit creation. Fistulas may be identified using dye or imaging with a loopogram and looposcopy. Correction of obstruction such as stomal stenosis or urinary diversion should be pursued to relieve pressure off the conduit. Minimally invasive management such as fulguration can result temporary relief; however, the recurrence rate is high.