Dermatofibrosarcoma protuberans (DFSP) is a locally aggressive fibroblastic neoplasm that commonly occurs in the trunk and extremities but rarely in the head and neck region. We report an atypical presentation of DFSP with fibrosarcomatous transformation of the parotid region. A 34-year-old gentleman presented with a huge left parotid swelling that progressively increased in size over the past seven years. He claimed that a biopsy of the swelling was done five years prior in another hospital and he was told it was benign. He defaulted to follow-up as the lesion was painless initially but it started to be painful and bleed intermittently one month before the presentation. Total parotidectomy was done with the removal of adjacent enlarged lymph nodes but histopathological evaluation of the samples showed fibrosarcomatous DFSP with positive margins. Unfortunately, the patient defaulted to follow-up again post-op and presented again after one year with extensive systemic metastasis. The dilemmas in managing this case and suggestions for countermeasures together with references according to the relevant literature are discussed.