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A man aged 56 years with a history of ulcerative colitis (UC) status postsubtotal colectomy was hospitalised with fevers, dry cough, eye redness and a new bloody, mucoid rectal discharge. 2 months prior to admission, the dermatologist had started him on dapsone for subcorneal pustular dermatosis but did not recognise that he had recently self-discontinued mesalamine enemas, inducing a flare of his UC. After a thorough inpatient evaluation, including flexible sigmoidoscopy, active UC involving the rectal stump was determined to be driving his dermatological and ophthalmological findings. By reinstituting mesalamine enemas, control of his UC was achieved and the extraintestinal manifestations of his inflammatory bowel disease (IBD) resolved. This case illustrates the importance of careful history taking and of early recognition of extraintestinal manifestations of IBD in order to appropriately target treatment and prevent unnecessary morbidity.