D-Penicillamine is one of the diseases modifying medication used to treat Rheumatoid arthritis and Systemic sclerosis. In this article we have described two interesting cases of Dermatomyositis and Bullous pemphigoid secondary to D-Penicillamine. This article emphasizes the fact that D-Penicillamine remains as one of the effective and well-tolerated medications, however patients need close monitoring while on medication, so that uncommon side effects are recognized and treated promptly.