Objective: Assignment of the tumors into various cytological categories and to determine specific sub-typing in individual cases. To correlate the cytological features observed with histological parameters and analyse the reasons for discordant diagnosis. Materials and Methods: 27 cases, with both cytological and histopathological details, diagnosed as soft tissue tumors (STT) were included. The lesions were classified into 6 cytological categories. Results: On fine-needle aspiration cytology (FNAC), 14 cases were reported positive for malignant cells and 13 were reported as benign. On histological follow up discordant lesions were further characterized. Discordance was attributable largely to sampling in lipomatous lesions and interpretation errors due to inattention to clinical history, low volume of these lesions in practice, and overlapping cytomorphologic features with other entities. Sensitivity and specificity was 84.61% and 85.71% respectively and overall diagnostic accuracy was 85.18%. Conclusion: Soft tissue tumors are rare neoplasms that pose a significant challenge as a result of their morphologic overlap and biological heterogeneity. 'Time-honored' histopathology is recognized as the 'gold standard' for evaluation of STT. FNAC can be used as a diagnostic modality in soft tissue lesions due to its lesser cost, ease of performance, safety, along with reasonable specificity and sensitivity. In the current era, where 'needle is preceding the scalpel' and the biopsy material is getting limited, our study highlights the role and scope, diagnostic difficulties and pitfalls to be aware of when interpreting these challenging FNACs.