Automatic recognition of traffic signs in complex, real-world environments has become a pressing research concern with rapid improvements of smart technologies. Hence, this study leveraged an industry-grade object detection and classification algorithm (You-Only-Look-Once, YOLO) to develop an automatic traffic sign recognition system that can identify widely used regulatory and warning signs in diverse driving conditions. Sign recognition performance was assessed in terms of weather and reflectivity to identify the limitations of the developed system in real-world conditions. Furthermore, we produced several editions of our sign recognition system by gradually increasing the number of training images in order to account for the significance of training resources in recognition performance. Analysis considering variable weather conditions, including fair (clear and sunny) and inclement (cloudy and snowy), demonstrated a lower susceptibility of sign recognition in the highly trained system. Analysis considering variable reflectivity conditions, including sheeting type, lighting conditions, and sign age, showed that older engineering-grade sheeting signs were more likely to go unnoticed by the developed system at night. In summary, this study incorporated automatic object detection technology to develop a novel sign recognition system to determine its real-world applicability, opportunities, and limitations for future integration with advanced driver assistance technologies.