The Wyoming Highway Patrol (WHP) investigates more than 7,000 vehicle crashes yearly, often as first-hand responders. They often drive at high speeds through difficult road/weather conditions and under enormous secondary workloads, leading to an increased risk of crash. Connected vehicle (CV) technology can communicate timely road and traveler information messages (TIMs) to troopers, which could significantly reduce the frequency, severity, or both, of these crashes. The majority of the troopers, however, might not be familiar with driving a CV. This paper developed a “first responder-specific” training program on safe interaction with the technology and an in-depth assessment of how these new technologies are perceived by the troopers. The training program contains an E-training module and a hands-on driving simulator training module. The E-training presents concept of various CV warnings and notifications, including forward collision warning (FCW), spot weather warnings, work zone warnings, and other TIMs. Two scenarios were developed to familiarize troopers to simulated driving, two single-alert scenarios to help mastering the two most important warnings (FCW and variable speed limit), and two multiple-alert scenarios to train the troopers to drive in a comprehensive connected environment. A quiz section in the E-training module and comprehensive pre- and post-training questionnaire surveys were performed to evaluate the effectiveness of the developed CV training program. According to the trainees from the WHP, the driving simulator provided impressively realistic real-life-like scenarios for the troopers to practice the CV warnings they learned during the E-training.