For the potential safety benefits of driving automation systems to be fully realized, drivers must understand the capabilities and limitations of these systems. This study explored a range of materials that drivers may access when trying to learn about driving automation system safety features: owner’s manual only, owner’s manual and OEM website video or animation, and owner’s manual and MyCarDoesWhat.org videos. Three vehicles, a 2015 Infiniti Q50, a 2016 Honda CR-V, and a 2015 Chevy Tahoe, were selected to represent a range of vehicle types, sizes, technologies, and price points. Each training condition was tested with each vehicle for a total of nine possible testing scenarios. Thirty-six participants were recruited for the study, with an equal number of males and females from two age groups, 25–39 and 40–54 years old. Participants were balanced across the nine possible testing scenarios. A two-part study was conducted to assess participants’ ability to learn from existing training materials and to determine how well participants were able to retain what they learned. When taking into consideration participants’ self-reported learning styles, average scores across all technologies were fairly comparable across style, and participants were able gain at least a rudimentary understanding of the operation and purposes of driving automation system technologies. However, participants were less sure of the specifics associated with the technologies (i.e., activation, alerts or warnings, and appropriate use). Those in the multimedia testing conditions reported feeling more familiar with the technologies than those in the owner’s manual only condition. Participants found the videos to be an entertaining and easier-to-understand alternative to the manual. Several indicated that they would refer to the video first to see how the technology worked and then refer to the manual to gain a more in-depth understanding. Videos with sound and additional details were preferred to the simpler animations.