As a critical fastener connecting steel rails, fish-tail bolts ensure the safety of railway transportation. To improve the efficiency of fish-tail bolt loosening detection, this paper proposes a computer vision-based method for detecting fish-tail bolt looseness under tilted perspectives. The method first identifies bolt positions and coordinates of corner points on rail clamp edges through object detection and key point detection. Then, considering diverse rail clamp dimensions and combining with bolt positions, it employs dual perspective transformations for image rectification. Finally, utilizing the Lightweight OpenPose network, angle recognition of key bolt edges is achieved through Gaussian ring-shaped smooth labels, with loosening determination made by comparing angular variations across temporal frames. In experimental validation, tests were first conducted on a public dial-reading dataset for pointer angle recognition, showing a minimum average error of only 0.8°, which verifies the algorithm’s feasibility. Subsequently, based on fish-tail bolt images captured under various tilted perspectives, we constructed a self-made dataset of bolt key edges and performed loosening detection experiments. For bolt images in boundary postures, after rotation preprocessing, the average detection error was reduced to 0.7°. When the loosening threshold was set to 2.1°, the detection accuracy reached 97%. Experimental results indicate that the proposed method effectively identifies fish bolt loosening, providing crucial technical reference for railway safety maintenance.