Crohn's disease is difficult to manage and often requires multiple medications. While these drugs vastly improve quality of life, physicians must monitor for adverse events. We report a case of a flare of inverse psoriasis after 15 months of treatment with ustekinumab. This is the third reported case of a flare of drug-induced psoriasis with ustekinumab, and it is the first reported case with an inverse presentation; however, the clinical picture is confounded by concomitant use of hydroxychloroquine. Inverse psoriasis is a rare variant of drug-induced psoriasis of which physicians must be cognizant while treating patients with Crohn's disease.