A traditional structural analysis of scaffolding structures requires loading conditions that are only possible during design, but not in operation. Thus, this study proposes a method that can be used during operation to make an automated safety prediction for scaffolds. It implements a divide-and-conquer technique with deep learning. As a test scaffolding, a four-bay, three-story scaffold model was used. Analysis of the model led to 1411 unique safety cases for the model. To apply deep learning, a test simulation generated 1,540,000 datasets for pre-training, and an additional 141,100 datasets for testing purposes. The cases were then sub-divided into 18 categories based on failure modes at both global and local levels, along with a combination of member failures. Accordingly, the divide-and-conquer technique was applied to the 18 categories, each of which were pre-trained by a neural network. For the test datasets, the overall accuracy was 99%. The prediction model showed that 82.78% of the 1411 safety cases showed 100% accuracy for the test datasets, which contributed to the high accuracy. In addition, the higher values of precision, recall, and F1 score for the majority of the safety cases indicate good performance of the model, and a significant improvement compared with past research conducted on simpler cases. Specifically, the method demonstrated improved performance with respect to accuracy and the number of classifications. Thus, the results suggest that the methodology could be reliably applied for the safety assessment of scaffolding systems that are more complex than systems tested in past studies. Furthermore, the implemented methodology can easily be replicated for other classification problems.