Herpes zoster (HZ) is caused by the reactivation of the varicella zoster virus and presents with painful vesicular lesions in a dermatomal distribution. Disseminated HZ occurs when skin lesions erupt in numerous dermatomes. Upadacitinib is the first oral medication approved to treat moderate-severe Crohn's disease and has been associated with nonsevere cases of HZ. We present a case of a 60-year-old woman with refractory Crohn's disease who failed multiple immunosuppressive therapies, completed the recombinant zoster vaccines, and developed disseminated HZ on high-dose upadacitinib. She was treated with intravenous acyclovir, upadacitinib was discontinued, and was discharged on suppressive valacyclovir.