The human immunodeficiency virus (HIV) is known to cause altered disease presentations. We present here, the case of a 14-year-old boy who came to us with a chronic, painful, nonhealing ulcer of 4 months duration over the dorsum of right hand. Before our observation, he was variably diagnosed and treated as atypical mycobacterial infection, deep fungal infection, squamous cell carcinoma, and pyoderma gangrenosum. On administration of systemic corticosteroids his condition worsened, after which he was tested for, and found to be HIV positive. He was put onto valacyclovir, responded slowly, with healing after 2 months of antiviral therapy. The case report highlights unusual presentation in an under-considered age group and a slow response to otherwise effective therapy.