Microsurgical free-tissue transfer has been a safe option for tissue reconstruction. This study aimed to analyze the diagnostic accuracy of hyperspectral imaging (HSI) after free-tissue transfer surgery. From January 2017 to October 2019, 42 consecutive free-flap surgeries were performed, and their outcomes were analyzed via HSI. Clinical examination of free-flap perfusion was initially performed. Clinical examination findings were subsequently compared with those of HSI. Potential venous congestion with subsequent necrosis was defined as a tissue hemoglobin index of ≥53%. Student's t-test was used to compare the results of the analysis. The evaluation of sensitivity and specificity for flap failure detection was time dependent using the Fisher's exact test. A p-value of ≤0.05 was considered statistically significant. Microsurgical tissue transfer success rate was 84%. Seven patients presented with venous congestion that caused total flap necrosis. Overall, 124 assessments were made. HSI accurately identified 12 out of 19 pathological images: four as false positive and seven as false negative. The sensitivity and specificity of HSI were 57 and 94%, respectively, compared to those of clinical examination that were 28 and 100%, respectively, within 24 h following tissue transfer. The sensitivity and specificity of HSI were 63 and 96%, respectively, compared to those of clinical examination that were 63 and 100%, respectively, within the first 72 h. A tissue hemoglobin index of ≥53% could predict venous congestion after free-flap surgery. HSI demonstrated higher sensitivity than clinical examination within the first 24 h; however, it was not superior compared to clinical findings within 72 h.