Collisions between trucks and vulnerable road users (VRUs) represent one of the most severe types of road collisions. Research initiatives to mitigate truck–VRU collisions include vehicle redesign, infrastructure improvements, and driver warning systems. Truck driver training is a complementary solution that can lead to improved driving behavior and collision reduction. We aimed to understand the perceptions of subject matter experts of current truck driver training in Ontario, Canada, to identify gaps and potential improvements, particularly targeting VRU safety in urban areas. Further, we investigated the degree to which VRU safety is covered and the potential to incorporate it in training through simulators. We conducted semi-structured interviews with 21 truck driver trainees, novice and experienced truck drivers, a driving instructor, and road safety professionals. The participants highlighted a notable gap between current training and real-world truck driving. VRU safety and hazard anticipation training emerged as a missing component in training. Nine out of 11 participants who received simulator training perceived it positively and recommended it for its safe and relatively realistic environment. The main topics that should be incorporated in VRU safety training, as recommended by interviewees, include training on difficult truck maneuvers with presence of VRUs, anticipating hazardous VRU actions, and navigating difficult infrastructure components. This work presents subject matter expert perceptions of current truck driver training in Ontario, Canada, and identifies gaps and improvements targeting VRU safety. Although the study is based on Ontario, the results can apply across Canada and beyond, where trucks pose dangers to VRUs.