Cylindromas are benign tumours arising as small, solitary, slow-growing nodules on the head and neck. Multiple cylindromas may form a 'turban tumour' in the autosomal dominant Brooke-Spiegler syndrome. We report two unusual cases of multiple cylindromas with transformation into cylindrocarcinomas. The first patient, a 63-year-old white woman, developed a cylindrocarcinoma on pre-existing multiple cylindromas on her right shoulder. Eight months after resection she developed a lymph node metastasis in the right axilla. The second patient, a 68-year-old white woman, presented with multiple cylindromas of the scalp. One of these transformed into a cylindrocarcinoma, infiltrating the dura mater, with local recurrence 2 years after incomplete resection and postoperative radiation.