Background/Objectives: Lung and cardiovascular diseases are leading causes of mortality worldwide, yet early detection remains challenging due to the subtle symptoms. Digital clubbing, characterized by the bulbous enlargement of the fingertips, serves as an early indicator of these diseases. This study aims to develop an automated system for detecting digital clubbing using deep-learning models for real-time monitoring and early intervention. Methods: The proposed system utilizes the YOLOv8 model for object detection and U-Net for image segmentation, integrated with the ESP32-CAM development board to capture and analyze finger images. The severity of digital clubbing is determined using a custom algorithm based on the Lovibond angle theory, categorizing the condition into normal, mild, moderate, and severe. The system was evaluated using 1768 images and achieved cloud-based and real-time processing capabilities. Results: The system demonstrated high accuracy (98.34%) in real-time detection with precision (98.22%), sensitivity (99.48%), and specificity (98.22%). Cloud-based processing achieved slightly lower but robust results, with an accuracy of 96.38%. The average processing time was 0.15 s per image, showcasing its real-time potential. Conclusions: This automated system provides a scalable and cost-effective solution for the early detection of digital clubbing, enabling timely intervention for lung and cardiovascular diseases. Its high accuracy and real-time capabilities make it suitable for both clinical and home-based health monitoring.