Onychotillomania, or nail-picking disorder, is an uncommon and misdiagnosed behavioral pattern focused on the nail apparatus. It is demarcated by the compulsive or irresistible urge in patients to constantly injure their own nails, with the fingers or tools, inflicting noticeable or even irreversible self-destruction of the nail unit. Despite its rarity, this self-injurious coercion often poses a diagnostic and therapeutic challenge. Not only do many patients deny nail manipulation, but also the disorder has long been recognized to present itself with a wide range of clinical features, which hampers early and indisputable diagnosis. Furthermore, onychotillomania constitutes a persistent and hardly manageable problem, mostly because of its psychocutaneous nature as well as its high propensity to coexist with underlying neuropsychiatric illnesses or other behavioral disorders. However, the medical literature concerning obsessive nail picking still remains relatively scarce. Herein, we present an extraordinary, yet very intriguing case of a Caucasian patient with onychotillomania and onychophagia coexistence masquerading a weird inflammation-like lesion.