Currently, students acquire driving skills by practicing in actual traffic conditions and through direct interactions with an instructor. While one-on-one interactions could be tailored to a student’s learning style and skill level, making them effective for learning, one-on-one interactions are also inefficient, potentially costly, and not standardized with limitations on which traffic situation can be safely taught. For these exact reasons Way AS has developed and commercially deployed a virtual driving instructor that educates students in high-fidelity simulators. In this paper, we present a module, the Lesson generator, that extends the virtual driving instructor to generate personalized lessons for individual students with the goal to practice in a focused and deliberately fashion the skills that need practice for the students to become proficient drivers. A case study is presented, and the path to deployment is discussed.