One focus of the U.S. Federal Motor Carrier Safety Administration (FMCSA) is to provide leadership in the testing and evaluation of promising safety technologies developed for use in commercial motor vehicles (CMVs). To this end, a program was developed by FMCSA to conduct independent, short-turnaround evaluations of promising safety technologies. In a nutshell, vendors who have promising safety technologies, focused in the commercial vehicle domain, are solicited to participate and submit an application. One technology is selected by FMCSA for each evaluation cycle (lasting approximately 18 months). The technology is tested in both static and dynamic conditions, after which a trucking fleet, and their drivers, are brought in to test the technology in a field operational test (FOT) lasting approximately 6 weeks. During the FOT, 15–20 trucks are instrumented with the technology and other data collection equipment, including sensors and video cameras. A naturalistic study is then conducted whereby drivers use the technology in their revenue-producing operations. Initially, often for the first 2 months, the technology collects data but does but not actively present alerts to the driver. Following this baseline period, a four-month intervention period is conducted. Each evaluation has resulted in more than 1,000,000 km of driving data including continuous video data. Data analyses focus on understanding the efficacy of the technology in terms of (i) safety improvements, (ii) challenges to implementation (e.g., unintended consequences), and (iii) user acceptance (including driver, fleet manager, and other fleet personnel as appropriate). The technology vendors who applied for the first three evaluations can be classified into the following general categories: fatigue/drowsiness, fleet management, visibility safety systems, cell phone policy/enforcement, and other. Three technology evaluations have thus far been completed with assessments of (i) a blind spot detection and warning system, (ii) an onboard monitoring system, and (iii) a novel mirror technology. High-level results of each of these three evaluations are highlighted in the paper.