Due to the significant threat to forest health posed by beetle infestations on pine trees, timely and accurate predictions are crucial for effective forest management. This study developed a pine tree stress probability prediction workflow based on monthly cloud-free Sentinel-2 composite images to address this challenge. First, representative pine tree stress samples were selected by combining long-term forest disturbance data using the Continuous Change Detection and Classification (CCDC) algorithm with high-resolution remote sensing imagery. Monthly cloud-free Sentinel-2 images were then composited using the Multifactor Weighting (MFW) method. Finally, a Random Forest (RF) algorithm was employed to build the pine tree stress probability model and analyze the importance of spectral, topographic, and meteorological features. The model achieved prediction precisions of 0.876, 0.900, and 0.883, and overall accuracies of 89.5%, 91.6%, and 90.2% for January, February, and March 2023, respectively. The results indicate that spectral features, such as band reflectance and vegetation indices, ranked among the top five in importance (i.e., SWIR2, SWIR1, Red band, NDVI, and NBR). They more effectively reflected changes in canopy pigments and leaf moisture content under stress compared with topographic and meteorological features. Additionally, combining long-term stress disturbance data with high-resolution imagery to select training samples improved their spatial and temporal representativeness, enhancing the model’s predictive capability. This approach provides valuable insights for improving forest health monitoring and uncovers opportunities to predict future beetle outbreaks and take preventive measures.