Abnormal loss of bone in the external auditory canal (EAC) constitutes an underreported condition in paleopathology. Thus far, all reported cases were diagnosed as the result of an external ear canal cholesteatoma (EACC). Here, we report two cases from the medieval period in Germany that show enlarged EACs with perforations of the anterior and posterior EAC walls. The cases were studied macroscopically, with a digital stereo microscope and by conventional X‐ray and computed tomography (CT)‐imaging techniques. In Case 1, the resorption caused a “ballooning” of the EAC while signs of osteonecrosis were missing. We therefore conclude that keratosis obturans (KO) is the most likely diagnosis. In Case 2, the periantral region adjacent to the perforations of the posterior EAC wall exhibits large resorption cavities and sequestrum‐like structures, indicative of osteonecrosis. In this case, we arrive at the diagnosis EACC. Ear diseases encompass a broad spectrum of conditions, many of them with potentially severe impacts on past people. It is therefore suggested to address ear diseases more frequently in paleopathology. Thus far, only a very limited number of entities of ear diseases have been diagnosed in paleopathological studies, and no case of KO has been reported. The present study thus expands the spectrum of paleo‐otopathological diagnoses.