Camera/Video Imaging Systems (C/VISs) help drivers monitor the areas around their truck by relaying live video images collected from cameras mounted on the truck’s exterior to monitors mounted inside the truck’s cabin. The purpose of this study was to expand on the favorable results from previous C/VIS test-track research performed by NHTSA and FMCSA by evaluating the implementation of C/VISs in a real-world operation. Drivers’ performance with and without a C/VIS was unobtrusively recorded using a naturalistic driving study approach. Twelve drivers from a fleet company participated in this research and drove a company truck on revenue producing routes. Each driver drove one truck that had either a commercially-available C/VIS, or an Advanced-C/VIS (A-C/VIS) developed by VTTI. The commercially-available C/VIS selected was called SIDETRACKERTM and had a side-view camera on each fender. The A-C/VIS had side-view cameras, a rear-view camera, and night-vision capabilities. The trucks that were driven in this study remained permanently coupled to 48-ft long trailers over the course of the twelve-month data-collection interval. Each driver drove a truck for one month with the C/VIS disabled (Baseline condition), and three months with the C/VIS enabled (Test condition). Drivers completed surveys regarding their driving performance and overall experience with C/VISs every two weeks. It was found that C/VISs are able to assist commercial motor vehicle (CMV) drivers in their daily driving task without deteriorating their driving performance. Specifically, the probability that drivers looked forward, their clearance to an adjacent vehicle when changing lanes, and their involvement in safety critical events (SCEs), did not change when driving with a C/VIS. Drivers also reported that the CVIS improved their awareness of surrounding objects and assisted them in performing lane changes and merge maneuvers, particularly when making right lane changes. The A-C/VIS’s rear-view vantage point was the most frequently used feature and was highly rated by drivers. Even though drivers’ positive subjective ratings can contribute to safety, it is important to note that drivers did not encounter fewer SCEs when driving with a C/VIS. A potential limitation with the study is that the driving data were collected when traffic density was low. Further research could observe drivers’ performance with and without C/VISs in congested traffic. Performance in dense traffic could provide a continued analysis of the distribution of SCE’s as an index of safety benefit. OEMs and tier-1 suppliers have developed multiple methods to implement C/VISs. The A-CVIS is an innovative approach to C/VIS that assists drivers to overcome blind spots; this paper presents a real-world evaluation of such a system including the identification of potential safety benefits.