Onychotillomania represents an unusual dermatosis affecting the nail unit. The term refers to ‘neurotic picking at a nail until it is permanently altered’. It can be difficult for dermatologists to diagnose, as typically patients will deny the self-destructive behavior and the clinical features may mimic other inflammatory conditions affecting the nail unit. Aside from the difficulty in establishing the diagnosis clinically, the histopathologic features of onychotillomania are nonspecific. With this limited knowledge, dermatopathologists could have difficulty in correlating the clinical and histopathologic features and determining the correct diagnosis. Establishing the diagnosis is critical, as onychotillomania is sometimes associated with major depression and obsessive-compulsive disorder, and can be a clue to uncovering these debilitating psychiatric disorders. Here we present two cases of onychotillomania and emphasize the clinical-pathological confrontation necessary to secure the diagnosis.