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Alcohol use disorder and gastric bypass surgery are highly comorbid. Alcohol withdrawal syndrome (AWS) is a common and potentially life-threatening event, requiring nuanced and individually tailored management depending on various clinical factors including patient history, alcohol consumption, comorbidities, and timeline of use. Although increasingly common, the literature for managing alcohol withdrawal in the gastric bypass population is quite limited. We present the case of a 45-year-old woman with a past history of Roux-en-Y gastric bypass admitted for alcohol withdrawal at a psychiatric hospital who experienced a complicated withdrawal despite adhering to standard management guidelines. She had been consuming 8 to 12 standard drinks daily, and she was therefore monitored on a Clinical Institute Withdrawal Assessment for Alcohol. She experienced only minimal withdrawal symptoms up to 48 hours following cessation of alcohol consumption. At 70 hours postcessation, she experienced a witnessed tonic-clonic seizure with associated head trauma with internal bleeding, requiring acute medical intervention. This timeline of withdrawal symptoms is atypical, yet perhaps understood in the context of her past medical history which included gastric bypass surgery. We discuss the potential complicating factors inherent in individuals who have received Roux-en-Y gastric bypass in the past with respect to alcohol metabolism. We discuss the similar considerations with respect to altered metabolism of therapeutics commonly used in managing this condition. Lastly, we include a review of the extent literature on this topic and propose possible considerations for managing this unique but increasingly prevalent clinical scenario.