Malignant solitary fibrous tumors (SFTs) are extremely uncommon and poorly understood mesenchymal neoplasms. There are only rare published accounts of the cytopathologic features of these tumors, prompting the current study. All cases of malignant SFT with preoperative fine-needle aspirations (FNAs) from 1999 to 2008 were retrieved from the archives of 3 large teaching hospitals. FNA smears and cell block material including immunoperoxidase stains were reviewed, and the cytologic characteristics were described. Thirteen cases of malignant SFT were identified in 11 patients. Mean age was 58 years, with a men:women ratio of 1:2.6. The tumors were generally large, with a mean size of 13.4 cm. Cytomorphologic features included mostly hypercellular smears with tissue fragments of monotonous, plump spindled cells with blunt-ended and indented nuclei and fragile, wispy cytoplasm. Also seen were bare nuclei, occasional mitoses, and rare necrosis. Some cases showed a predominance of epithelioid cells, whereas others displayed a loose myxomatous matrix. There was a general lack of single cells. None of the cases was diagnosed accurately as malignant SFT on FNA, and only 6 cases were called malignant or suspicious for malignancy. The FNA diagnosis of malignant SFT is extremely difficult and needs histologic material for accurate interpretation. Predominant FNA diagnoses were SFT or spindle cell neoplasm. Malignant SFT must be included in the differential diagnosis of a spindle cell neoplasm of any anatomic site, particularly if it displays features not typical of benign SFT. Immunoperoxidase staining has some utility, mainly in ruling out other neoplasms in the differential diagnosis. (c) 2010 American Cancer Society.