This paper investigates the use of deep transfer learning based on convolutional neural networks (CNNs) to monitor the condition of bolted joints using acoustic emissions. Bolted structures are critical components in many mechanical systems, and the ability to monitor their condition status is crucial for effective structural health monitoring. We evaluated the performance of our methodology using the ORION-AE benchmark, a structure composed of two thin beams connected by three bolts, where highly noisy acoustic emission measurements were taken to detect changes in the applied tightening torque of the bolts. The data used from this structure is derived from the transformation of acoustic emission data streams into images using continuous wavelet transform, and leveraging pretrained CNNs for feature extraction and denoising. Our experiments compared single-sensor versus multiple-sensor fusion for estimating the tightening level (loosening) of bolts and evaluated the use of raw versus prefiltered data on the performance. We particularly focused on the generalization capabilities of CNN-based transfer learning across different measurement campaigns and we studied ordinal loss functions to penalize incorrect predictions less severely when close to the ground truth, thereby encouraging misclassification errors to be in adjacent classes. Network configurations as well as learning rate schedulers are also investigated, and super-convergence is obtained, i.e., high classification accuracy is achieved in a few number of iterations with different networks. Furthermore, results demonstrate the generalization capabilities of CNN-based transfer learning for monitoring bolted structures by acoustic emission with varying amounts of prior information required during training.