We report on two female patients (age 78 and 81) suffering from multiple hereditary cylindromas which had grown, changed in color towards a bluish note, and partly exulcerated. The lesions were widely excised; plastic surgical reconstruction resulted in satisfactory healing. Histological examination showed similar features in both patients: We observed decreased differentiation of structures otherwise typical for cylindromas, polymorphism of cells and nuclei, mitoses, and beginning infiltration of the galea. Although there were no metastases found, malignant transformation was deduced from sudden growth, exulceration, as well as dedifferentiation of histological structures in combination with infiltrative expansion.