Objective: Procedures for diagnosing bone tumors should be rapid and minimally invasive. Thus, cytological examinations are more useful for such purposes than histological examinations. In order to identify cytomorphological findings that could be used to diagnose bone metastasis from gastrointestinal stromal tumors (GIST), previous cases were reviewed. Study Design: Cytological samples of 7 lesions from 4 patients with GIST-derived bone metastasis, which were obtained from 2001 to 2017 at the JFCR Cancer Institute Hospital, were reviewed. Results: The metastasis of GIST to the bone was clinically suspected before the cytological and histological examinations in all cases since they all involved other metastatic lesion(s), and characteristic osteolytic lesions were detected on radiological images. Although various cell shapes were encountered, spindle cell proliferation was seen in all cytological samples. No pleomorphism was apparent. Characteristic nuclear findings were observed. All of the cases could be diagnosed as GIST-derived bone metastasis. Conclusion: GIST-derived bone metastasis can be diagnosed by examining cytological samples.