Machine learning techniques have progressively emerged as important and reliable tools that, when combined with machine condition monitoring, can diagnose faults with even superior performance than other condition-based monitoring approaches. Furthermore, statistical or model-based approaches are often not applicable in industrial environments with a high degree of customization of equipment and machines. Structures such as bolted joints are a key part of the industry; therefore, monitoring their health is critical to maintaining structural integrity. Despite this, there has been little research on the detection of bolt loosening in rotating joints. In this study, vibration-based detection of bolt loosening in a rotating joint of a custom sewer cleaning vehicle transmission was performed using support vector machines (SVM). Different failures were analyzed for various vehicle operating conditions. Several classifiers were trained to evaluate the influence of the number and location of accelerometers used and to determine the best approach between specific models for each operating condition or a single model for all cases. The results showed that using a single SVM model with data from four accelerometers mounted both upstream and downstream of the bolted joint resulted in more reliable fault detection, with an overall accuracy of 92.4%.