Computer-based, cognitive training procedures aim to increase safety by improving skills related to driving, such as speed-of-processing and the Useful Field of View. The current study assessed the effectiveness of DriveSharp in training older drivers in a naturalistic class setting. Participants (n = 24) attended 10 hours of DriveSharp classes over 5 weeks. Pre- and post-testing sessions assessed improvements on a dynamic hazard perception test, Trails A and Trails B. A control group (n = 18) completed only pre- and post-testing sessions. In-class training times were lower than expected. Participants’ improvement in the games leveled off after the first assessment and the DriveSharp group did not demonstrate a significant improvement in performance compared to the control group. Among several usability issues, the most problematic were misunderstanding task goals and the difference between training and evaluation. There are several implications for those using DriveSharp to enhance older drivers’ safety.