Postoperative free flap monitoring is a critical part of reconstructive microsurgery. Postoperative clinical assessments rely heavily on specialty-trained staff. Therefore, in regions with limited specialist availability, the feasibility of performing microsurgery is restricted. This study aimed to apply artificial intelligence in postoperative free flap monitoring and validate the ability of machine learning in predicting and differentiating types of postoperative free flap circulation. Postoperative data from 176 patients who received free flap surgery were prospectively collected, including free flap photographs and clinical evaluation measures. Flap circulation outcome variables included normal, arterial insufficiency, and venous insufficiency. The Synthetic Minority Oversampling Technique plus Tomek Links (SMOTE-Tomek) was applied for data balance. Data were divided into 80%:20% for model training and validation. Shapley Additive Explanations were used for prediction interpretations of the model. Of 805 total included flaps, 555 (69%) were normal, 97 (12%) had arterial insufficiency, and 153 (19%) had venous insufficiency. The most effective prediction model was developed based on random forest, with an accuracy of 98.4%. Temperature and color differences between the flap and the surrounding skin were the most significant contributing factors to predict a vascular compromised flap. This study demonstrated the reliability of a machine-learning model in differentiating various types of postoperative flap circulation. This novel technique may reduce the burden of free flap monitoring and encourage the broader use of reconstructive microsurgery in regions with a limited number of staff specialists.