Retronychia is a clinical condition resulting from embedding of the nail plate into the proximal nail fold. We report two adolescent girls, 14 and 16 years of age, with a history of chronic proximal paronychia of the great toe, one of them developing osteomyelitis. After failure of treatment with several systemic antibiotics, nail avulsion was performed, leading us to the diagnosis of retronychia and with rapid and complete resolution of symptoms in both cases. Delay in diagnosis of retronychia can lead to local complications and prolonged discomfort.