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Background/Objectives: Driving cessation is associated with adverse health outcomes. Proactive support that extends safe driving while preparing for life after driving cessation has been emphasized, but empirical evidence remains limited. This study examined the effects of a proactive class for older drivers on awareness and behavior related to driving and mobility (Study 1) and on longitudinal changes in on-road driving behavior (Study 2). Methods: The proactive class was implemented as a municipal program, including information provision, training activities, group discussions, and optional on-road driving evaluations. Study 1 included 71 older drivers who attended the class at least five times annually and completed an anonymous questionnaire assessing perceived changes in awareness and behavior. Study 2 included 29 participants who completed standardized on-road driving evaluations at baseline and at a 1-year follow-up. Paired t tests or Wilcoxon signed-rank tests with effect sizes were applied. Results: In Study 1, participants reported increased awareness of safe driving, greater confidence in continuing to drive, heightened risk perception, initiation of health-related behaviors, trial use of public transportation, and increased healthcare utilization, particularly ophthalmology visits. In Study 2, total scores on the on-road driving skill test improved significantly at follow-up (Cohen’s dz = 0.805), with reductions in errors related to braking, vehicle control, and overspeeding. No significant changes were observed in physical, cognitive, or daily functioning, except for a reduction in driving simulator accidents. Conclusions: A proactive, continuous driving transition support class may facilitate multidimensional behavioral change and improve on-road driving performance among older drivers, supporting safer mobility and healthier aging. This study provides an initial conceptual and empirical foundation for proactive driving transition support delivered during the driving continuation phase, which will be examined in a future randomized controlled trial.