Innovative wood inspection technology is crucial in various industries, especially for determining wood quality by counting rings in each stave, a key factor in wine barrel production. (1) Background: Traditionally, human inspectors visually evaluate staves, compensating for natural variations and characteristics like dirt and saw-induced aberrations. These variations pose significant challenges for automatic inspection systems. Several techniques using classical image processing and deep learning have been developed to detect tree-ring boundaries, but they often struggle with woods exhibiting heterogeneity and texture irregularities. (2) Methods: This study proposes a hybrid approach combining classical computer vision techniques for preprocessing with deep learning algorithms for classification, designed for continuous automated processing. To enhance performance and accuracy, we employ a data augmentation strategy using cropping techniques to address intra-class variability in individual staves. (3) Results: Our approach significantly improves accuracy and reliability in classifying wood with irregular textures and heterogeneity. The use of explainable AI and model calibration offers a deeper understanding of the model’s decision-making process, ensuring robustness and transparency, and setting confidence thresholds for outputs. (4) Conclusions: The proposed system enhances the performance of automatic wood inspection technologies, providing a robust solution for industries requiring precise wood quality assessment, particularly in wine barrel production.