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Introduction: The clinical course of patients who present to the emergency department (ED) with urinary retention is usually uneventful. In this case, we explore the life-threatening complications of urinary retention and bladder decompression. Case Report: We report the case of a 57-year-old man who presented to the ED with difficulty voiding. A urinary catheter was placed. The patient had severe post-obstructive diuresis. He developed hematuria and became hypotensive. After aggressive resuscitation, including blood products, the patient required operative intervention for hemorrhage control. Conclusion: Clinicians should be aware of and be able to manage the rare but life-threatening complications associated with urinary retention.