Retronychia is a frequently misdiagnosed nail disorder characterized by proximal ingrowth of the nail into the proximal nail plate. Often presenting with chronic paronychia, retronychia is commonly misdiagnosed and treated ineffectively with antimicrobials. The main cause is repeated micro-trauma to the affected nail, therefore a thorough history of exposures and insults to the toenail is crucial in identifying the cause of this nail abnormality. Herein, we describe a case of a UPS employee who presented with a painful nail after dropping a package on her foot that was unresponsive to medical treatment for 2 years. This case highlights the importance of taking a thorough history and physical examination for diagnosing retronychia.